UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 10-Q

☑	QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the Quarterly Period Ended ~~March~~June 3130, 2021

☐	TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the Transition Period from____to____

Commission File Number 001-35506

PROOFPOINT, INC.

(Exact name of registrant as specified in its charter)

Delaware		51-0414846
(State or other jurisdiction of incorporation or organization)		(I.R.S. Employer Identification No.)
925 West Maude Avenue Sunnyvale, California		94085
(Address of principal executive offices)		(Zip Code)

(408) 517-4710

(Registrant’s telephone number, including area code)

Securities registered pursuant to Section 12(b) of the Act:

Title of each class	Trading Symbol(s)	Name of each exchange on which registered
Common Stock , $0.0001 par value per share,	PFPT	Nasdaq Global Select Market
Common Stock, $0.0001 par value per share	PFPT	Nasdaq Global Select Market

Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Sections 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☑No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☑ No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, or a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer”, “smaller reporting company” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer	☑	Accelerated filer	☐
Non-accelerated filer	☐	Smaller reporting company	☐
		Emerging growth company	☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐ No ☑

Shares of Proofpoint, Inc. common stock, $0.0001 par value per share, outstanding as of ~~April~~July 15, 2021: 57,~~369~~757,~~765~~909 shares.

Table of Contents

TABLE OF CONTENTS

		Page
PART I. FINANCIAL INFORMATION
ITEM 1. FINANCIAL STATEMENTS (UNAUDITED):		3
Condensed Consolidated Balance Sheets as of March 31, 2021 and December 31, 2020		3
Condensed Consolidated Balance Sheets as of June 30, 2021 and December 31, 2020		3
Condensed Consolidated Statements of Operations for the Three Months Ended March 31, 2021 and 2020		4
Condensed Consolidated Statements of Operations for the Three and Six Months Ended June 30, 2021 and 2020		4
Condensed Consolidated Statements of Comprehensive Loss for the Three Months Ended March 31, 2021 and 2020		5
Condensed Consolidated Statements of Comprehensive Loss for the Three and Six Months Ended June 30, 2021 and 2020		5
Condensed Consolidated Statements of Stockholders' Equity for the Three Months Ended March 31, 2021 and 2020		6
Condensed Consolidated Statements of Stockholders' Equity for the Three and Six Months Ended June 30, 2021 and 2020		6
Condensed Consolidated Statements of Cash Flows for the Three Months Ended March 31, 2021 and 2020		7
Condensed Consolidated Statements of Cash Flows for the Six Months Ended June 30, 2021 and 2020		8
Notes to Condensed Consolidated Financial Statements		910
ITEM 2. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS		2728
ITEM 3. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK		4041
ITEM 4. CONTROLS AND PROCEDURES		4142
PART II. OTHER INFORMATION
ITEM 1. LEGAL PROCEEDINGS		4243
ITEM 1A. RISK FACTORS		4243
ITEM 2. UNREGISTERED SALES OF EQUITY SECURITIES AND USE OF PROCEEDS		6364
ITEM 3. DEFAULTS UPON SENIOR SECURITIES		6365
ITEM 4. MINE SAFETY DISCLOSURES		6365
ITEM 5. OTHER INFORMATION		6365
ITEM 6. EXHIBITS		6466
SIGNATURES		6567

Table of Contents

PART I. FINANCIAL INFORMATION

ITEM 1. FINANCIAL STATEMENTS.

Proofpoint, Inc.

Condensed Consolidated Balance Sheets

(In thousands, except per share amounts)

(Unaudited)

	March 31, 2021			December 31, 2020
	June 30, 2021			December 31, 2020
Assets
Current assets:
Cash and cash equivalents	$	~~882~~929,~~550~~306		$	910,279
Accounts receivable, net		~~180~~204,~~971~~264			255,390
Inventory		~~457~~432			317
Deferred product costs		3,~~466~~255			3,480
Deferred commissions		5962,~~191~~680			57,779
Prepaid expenses and other current assets		3335,~~110~~889			32,493
Total current assets		1,~~159~~235,~~745~~826			1,259,738
Property and equipment, net		107,~~692~~126			111,030
Operating lease right-of-use assets		~~182~~179,~~728~~001			182,228
Long-term deferred product costs		~~394~~464			420
Goodwill		738,037			688,454
Intangible assets, net		~~131~~116,~~303~~567			130,392
Long-term deferred commissions		~~110~~118,~~181~~808			108,762
Other assets		2215,~~456~~916			17,686
Total assets	$	2,~~452~~511,~~536~~745		$	2,498,710
Liabilities and Stockholders’ Equity
Current liabilities:
Accounts payable	$	229,~~407~~804		$	2,233
Accrued liabilities		~~112~~128,~~931~~779			132,187
Operating lease liabilities		3237,~~961~~573			28,560
Deferred revenue		~~704~~703,~~890~~029			702,248
Total current liabilities		~~853~~899,~~189~~185			865,228
Convertible senior notes		907,~~037~~991			906,084
Long-term operating lease liabilities		~~177~~173,~~110~~161			178,506
Other long-term liabilities		3941,~~606~~092			39,639
Long-term deferred revenue		~~183~~205,~~598~~910			190,032
Total liabilities		2,~~160~~227,~~540~~339			2,179,489
Commitments and contingencies (Note 7)
Stockholders’ equity:
Convertible preferred stock, $0.0001 par value; 5,000 shares authorized; no shares issued and outstanding		—			—
Common stock, $0.0001 par value; 200,000 shares authorized; 58,949 shares issued and 57,406 shares outstanding at March 31, 2021; 58,513 shares issued and 57,178 shares outstanding at December 31, 2020		6			6
Common stock, $0.0001 par value; 200,000 shares authorized; 59,396 shares issued and 57,717 shares outstanding at June 30, 2021; 58,513 shares issued and 57,178 shares outstanding at December 31, 2020		6			6
Additional paid-in capital		1,~~351~~414,~~655~~846			1,307,474
Treasury stock, at cost; 1,543 shares and 1,335 shares at March 31, 2021 and December 31, 2020		(165,443	)		(139,356	)
Treasury stock, at cost; 1,679 shares and 1,335 shares at June 30, 2021 and December 31, 2020		(183,309	)		(139,356	)
Accumulated deficit		(~~894~~947,~~222~~137	)		(848,903	)
Total stockholders’ equity		~~291~~284,~~996~~406			319,221
Total liabilities and stockholders’ equity	$	2,~~452~~511,~~536~~745		$	2,498,710

See accompanying Notes to the Condensed Consolidated Financial Statements.

Table of Contents

Proofpoint, Inc.

Condensed Consolidated Statements of Operations

(In thousands, except per share amounts)

(Unaudited)

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
	2021			2020			2021			2020
Revenue:
Subscription	$	~~283~~303,~~612~~510		$	~~244~~254,~~069~~892		$	587,122		$	498,961
Hardware and services		45,~~219~~143			53,~~705~~546			9,362			9,251
Total revenue		~~287~~308,~~831~~653			~~249~~258,~~774~~438			596,484			508,212
Cost of revenue:(1)(2)
Subscription		6467,~~007~~659			59,~~848~~193			131,666			119,041
Hardware and services		9,~~513~~420			98,~~083~~382			18,933			17,465
Total cost of revenue		7377,~~520~~079			6867,~~931~~575			150,599			136,506
Gross profit		~~214~~231,~~311~~574			~~180~~190,~~843~~863			445,885			371,706
Operating expense:(1)(2)
Research and development		8081,~~518~~319			6970,~~895~~602			161,837			140,497
Sales and marketing		~~143~~142,~~144~~949			~~123~~116,~~162~~279			286,093			239,441
General and administrative		3254,~~711~~664			2914,~~555~~812			87,375			44,367
Total operating expense		~~256~~278,~~373~~932			~~222~~201,~~612~~693			535,305			424,305
Operating loss		(4247,~~062~~358	)		(4110,~~769~~830	)		(89,420	)		(52,599	)
Interest expense		(1,~~528~~533	)		(1,~~524~~525	)		(3,061	)		(3,049	)
Other income, net		365			4,621
Other (expense) income, net		(1,712	)		(1,092	)		(1,347	)		3,529
Loss before income taxes		(4350,~~225~~603	)		(3813,~~672~~447	)		(93,828	)		(52,119	)
Provision for income taxes		(2,~~094~~312	)		(281,~~169~~660	)		(4,406	)		(29,829	)
Net loss	$	(4552,~~319~~915	)	$	(6615,~~841~~107	)	$	(98,234	)	$	(81,948	)
Net loss per share, basic and diluted	$	(0.7992	)	$	(10.1726	)	$	(1.71	)	$	(1.43	)
Weighted average shares outstanding, basic and diluted		57,~~334~~479			5657,~~974~~369			57,406			57,168

(1) Includes stock-based compensation expense as follows:
Cost of subscription revenue	$	5,~~463~~933	$	5,~~542~~235		$	11,396	$	10,777
Cost of hardware and services revenue	$	1,~~612~~619	$	1,~~371~~408		$	3,231	$	2,779
Research and development	$	1718,~~717~~234	$	1516,~~605~~431		$	35,951	$	32,036
Sales and marketing	$	2723,~~263~~718	$	1817,~~519~~047		$	50,981	$	35,566
General and administrative	$	911,~~056~~779	$	10(3,~~528~~660	)	$	20,835	$	6,868

(2) Includes intangible amortization expense as follows:
Cost of subscription revenue	$	10,~~616~~719	$	9,~~938~~992	$	21,335	$	19,930
Sales and marketing	$	34,~~573~~017	$	43,~~513~~947	$	7,590	$	8,460

See accompanying Notes to the Condensed Consolidated Financial Statements.

Table of Contents

Proofpoint, Inc.

Condensed Consolidated Statements of Comprehensive Loss

(In thousands)

(Unaudited)

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
	2021			2020			2021			2020
Net loss	$	(4552,~~319~~915	)	$	(6615,~~841~~107	)	$	(98,234	)	$	(81,948	)
Other comprehensive income, net of tax:
Unrealized gain on short-term investments, net		—			4
Unrealized (loss) gain on short-term investments, net		—			(3	)		—			1
Comprehensive loss	$	(4552,~~319~~915	)	$	(6615,~~837~~110	)	$	(98,234	)	$	(81,947	)

See accompanying Notes to the Condensed Consolidated Financial Statements.

Table of Contents

Proofpoint, Inc.

Condensed Consolidated Statements of Stockholders’ Equity

(In thousands, except per share amounts)

(Unaudited)

	Three Months Ended March 31, 2021
	Three Months Ended June 30, 2021
	Common Stock					Additional Paid-In			Treasury Stock						Accumulated Other Comprehensive		Accumulated			Total Stockholders’
	Shares			Amount		Capital			Shares			Amount			Income (Loss)		Deficit			Equity
Balances at December 31, 2020		58,513		$	6	$	1,307,474			(1,335	)	$	(139,356	)	$	—	$	(848,903	)	$	319,221
Net loss		—			—		—			—			—			—		(45,319	)		(45,319	)
Stock-based compensation expense		—			—		57,209			—			—			—		—			57,209
Common stock issued		639			—		13,179			—			—			—		—			13,179
Tax withholding upon vesting of restricted stock awards		(203	)		—		(26,207	)		—			—			—		—			(26,207	)
Repurchase of common stock (Note 9)		—			—		—			(208	)		(26,087	)		—		—			(26,087	)
Balances at March 31, 2021		58,949		$	6	$	1,351,655			(1,543	)	$	(165,443	)	$	—	$	(894,222	)	$	291,996
Net loss		—			—		—			—			—			—		(52,915	)		(52,915	)
Stock-based compensation expense		—			—		57,034			—			—			—		—			57,034
Common stock issued		525			—		18,310			—			—			—		—			18,310
Tax withholding upon vesting of restricted stock awards		(78	)		—		(12,153	)		—			—			—		—			(12,153	)
Repurchase of common stock (Note 9)		—			—		—			(136	)		(17,866	)		—		—			(17,866	)
Balances at June 30, 2021		59,396		$	6	$	1,414,846			(1,679	)	$	(183,309	)	$	—	$	(947,137	)	$	284,406

	Three Months Ended March 31, 2020
	Three Months Ended June 30, 2020
	Common Stock					Additional Paid-In			Treasury Stock				Accumulated Other Comprehensive			Accumulated			Total Stockholders’
	Shares			Amount		Capital			Shares		Amount		Income (Loss)			Deficit			Equity
Balances at December 31, 2019		56,784		$	6	$	1,318,084			—	$	—	$	1		$	(725,594	)	$	592,497
Cumulative effect of adjustment from adoption of ASU 2020-06		—			—		(163,023	)		—		—		—			10,360			(152,663	)
Net loss		—			—		—			—		—		—			(66,841	)		(66,841	)
Unrealized gain on short-term investments		—			—		—			—		—		4			—			4
Stock-based compensation expense		—			—		47,975			—		—		—			—			47,975
Common stock issued		687			—		16,278			—		—		—			—			16,278
Tax withholding upon vesting of restricted stock awards		(211	)		—		(24,338	)		—		—		—			—			(24,338	)
Balances at March 31, 2020		57,260		$	6	$	1,194,976			—	$	—	$	5		$	(782,075	)	$	412,912
Net loss		—			—		—			—		—		—			(15,107	)		(15,107	)
Unrealized loss on short-term investments		—			—		—			—		—		(3	)		—			(3	)
Stock-based compensation expense		—			—		32,435			—		—		—			—			32,435
Issuance of restricted shares		11			—		—			—		—		—			—			—
Common stock issued		381			—		15,576			—		—		—			—			15,576
Tax withholding upon vesting of restricted stock awards		(64	)		—		(7,224	)		—		—		—			—			(7,224	)
Balances at June 30, 2020		57,588		$	6	$	1,235,763			—	$	—	$	2		$	(797,182	)	$	438,589

See accompanying Notes to the Condensed Consolidated Financial Statements.

Table of Contents

	Six Months Ended June 30, 2021
	Common Stock					Additional Paid-In			Treasury Stock						Accumulated Other Comprehensive		Accumulated			Total Stockholders’
	Shares			Amount		Capital			Shares			Amount			Income (Loss)		Deficit			Equity
Balances at December 31, 2020		58,513		$	6	$	1,307,474			(1,335	)	$	(139,356	)	$	—	$	(848,903	)	$	319,221
Net loss		—			—		—			—			—			—		(98,234	)		(98,234	)
Stock-based compensation expense		—			—		114,243			—			—			—		—			114,243
Common stock issued		1,164			—		31,489			—			—			—		—			31,489
Tax withholding upon vesting of restricted stock awards		(281	)		—		(38,360	)		—			—			—		—			(38,360	)
Repurchase of common stock (Note 9)		—			—		—			(344	)		(43,953	)		—		—			(43,953	)
Balances at June 30, 2021		59,396		$	6	$	1,414,846			(1,679	)	$	(183,309	)	$	—	$	(947,137	)	$	284,406

	Six Months Ended June 30, 2020
	Common Stock					Additional Paid-In			Treasury Stock				Accumulated Other Comprehensive		Accumulated			Total Stockholders’
	Shares			Amount		Capital			Shares		Amount		Income (Loss)		Deficit			Equity
Balances at December 31, 2019		56,784		$	6	$	1,318,084			—	$	—	$	1	$	(725,594	)	$	592,497
Cumulative effect of adjustment from adoption of ASU 2020-06		—			—		(163,023	)		—		—		—		10,360			(152,663	)
Net loss		—			—		—			—		—		—		(81,948	)		(81,948	)
Unrealized gain on short-term investments		—			—		—			—		—		1		—			1
Stock-based compensation expense		—			—		80,410			—		—		—		—			80,410
Issuance of restricted shares		11			—		—			—		—		—		—			-
Common stock issued		1,068			—		31,854			—		—		—		—			31,854
Tax withholding upon vesting of restricted stock awards		(275	)		—		(31,562	)		—		—		—		—			(31,562	)
Balances at June 30, 2020		57,588		$	6	$	1,235,763			—	$	—	$	2	$	(797,182	)	$	438,589

See accompanying Notes to the Condensed Consolidated Financial Statements.

Table of Contents

Proofpoint, Inc.

Condensed Consolidated Statements of Cash Flows

(In thousands)

(Unaudited)

	Three Months Ended March 31,
	Six Months Ended June 30,
	2021			2020
Cash flows from operating activities
Net loss	$	(4598,~~319~~234	)	$	(6681,~~841~~948	)
Adjustments to reconcile net loss to net cash provided by operating activities:
Depreciation and amortization		2448,~~033~~723			2346,~~470~~460
Stock-based compensation		61122,~~111~~394			5188,~~565~~026
Amortization of debt issuance costs and accretion of debt discount		953			949
Change in fair value of contingent consideration		(348	)		—
Amortization of deferred commissions		18,051			14,633
Amortization of debt issuance costs and accretion of debt discount		1,907			1,899
Noncash lease costs		7,920			6,426
Amortization of deferred commissions		37,272			30,003
Deferred income taxes		(147	)		(325	)
Noncash lease costs		15,651			12,918
Other		(260	)		(1,181	)
Deferred income taxes		(334	)		(692	)
Changes in assets and liabilities:
Other		1,399			268
Accounts receivable		76,074			93,453
Changes in assets and liabilities, net of effect of acquisitions:
Inventory		(140	)		872
Accounts receivable		52,365			92,062
Deferred product costs		40			(58	)
Inventory		(115	)		881
Deferred commissions		(20,882	)		(15,170	)
Deferred product costs		181			76
Prepaid expenses		1,034			(6,290	)
Deferred commissions		(52,220	)		(35,953	)
Other current assets		143			(282	)
Prepaid expenses		1,731			(6,773	)
Long-term assets		(278	)		(96	)
Other current assets		(172	)		(180	)
Accounts payable		(655	)		(6,017	)
Long-term assets		104			(59	)
Accrued liabilities		(14,335	)		14,720
Accounts payable		24,971			(9,513	)
Operating lease liabilities		(4,589	)		(7,159	)
Accrued liabilities		(3,283	)		20,122
Deferred revenue		(7,664	)		(10,495	)
Operating lease liabilities		(8,829	)		(13,561	)
Net cash provided by operating activities		95,090			92,174
Deferred revenue		12,787			(21,252	)
Net cash provided by operating activities		155,950			122,784
Cash flows from investing activities
Proceeds from maturities of short-term investments		—			3951,~~232~~187
Purchase of short-term investments		—			(19,876	)
Purchase of property and equipment		(612,~~615~~669	)		(1224,~~359~~149	)
Acquisition of businesses, net of cash acquired		(55,438	)		—
Receipts from escrow account		—			154
Net cash (used in) provided by investing activities		(62,053	)		6,997
Acquisitions of business, net of cash and restricted cash acquired		(55,438	)		(2,720	)
Net cash (used in) provided by investing activities		(68,107	)		4,596
Cash flows from financing activities
Proceeds from issuance of common stock		~~761~~19,083			218,~~966~~543
Withholding taxes related to restricted stock net share settlement		(2942,~~827~~238	)		(2735,~~600~~145	)
Repurchases of common stock		(2743,~~079~~953	)		—
Net cash used in financing activities		(5667,~~145~~108	)		(2416,~~634~~602	)
Effect of exchange rate changes on cash, cash equivalents and restricted cash		(~~582~~217	)		(~~907~~174	)
Net (decrease) increase in cash, cash equivalents and restricted cash		(23,690	)		73,630
Net increase in cash, cash equivalents and restricted cash		20,518			110,604
Cash, cash equivalents and restricted cash
Beginning of period		918,951			857,907
End of period	$	~~895~~939,~~261~~469		$	~~931~~968,~~537~~511
	Three Months Ended March 31,
	Six Months Ended June 30,
	2021			2020
Supplemental disclosure of noncash investing and financing activities
Unpaid purchases of property and equipment and asset retirement obligations	$	25,~~486~~977		$	46,~~789~~267
Operating lease right-of-use assets exchanged for lease obligations	$	812,~~311~~321		$	928,~~535~~195
Liability awards converted to equity	$	12,407		$	13,313

Table of Contents

	March 31, 2021		March 31, 2020
	June 30, 2021		June 30, 2020
Reconciliation of cash, cash equivalents and restricted cash as shown in the consolidated statement of cash flows
Cash and cash equivalents	$	~~882~~929,~~550~~306	$	~~921~~961,~~743~~356
Restricted cash included in prepaid expenses and other current assets		37,~~068~~578		3,~~223~~229
Restricted cash included in other non-current assets		92,~~643~~585		63,~~571~~926
Total cash, cash equivalents and restricted cash	$	~~895~~939,~~261~~469	$	~~931~~968,~~537~~511

See accompanying Notes to the Condensed Consolidated Financial Statements.

Table of Contents

Proofpoint, Inc.

Notes to Condensed Consolidated Financial Statements

(Unaudited)

(Dollars and share amounts in thousands, except per share amounts)

1. The Company and Summary of Significant Accounting Policies

The Company

Proofpoint, Inc. (“Proofpoint”, “we”, “us”, “our” or the “Company”) was incorporated in Delaware in June 2002 and is headquartered in California.

On April 25, 2021, the Company entered into an Agreement and Plan of Merger (the “Merger Agreement”) with Project Kafka Parent, LLC, a Delaware limited liability company (“Parent”), and Project Kafka Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Parent (“Merger Sub”), providing for the Company’s acquisition by affiliates of funds advised by private equity investment firm Thoma Bravo, L.P. (“Thoma Bravo”) in an all-cash transaction valued at approximately $12,300,000 (the “Transaction” or the “Merger”). If the Transaction is completed, the Company’s stockholders will be entitled to receive $176.00 in cash for each share of Proofpoint common stock they hold as of the effective time of the Transaction. The Transaction is expected to close in the third quarter of 2021, subject to approval by the Company’s stockholders and regulatory authorities and the satisfaction of customary closing conditions. See Note 14 “Subsequent Event” to the condensed consolidated financial statements in this Quarterly Report on Form 10-Q for information regarding the Merger.

Proofpoint is a leading security-as-a-service provider that enables large and mid-sized organizations worldwide to defend, protect, archive and govern their most sensitive data. The Company’s security-and compliance platform is comprised of an integrated suite of threat protection, information protection, and brand protection solutions, including email protection, advanced threat protection, email authentication, data loss prevention, SaaS application protection, response orchestration and automation, digital risk, web browser isolation, email encryption, archiving, eDiscovery, supervision, secure communication, phishing simulation and security awareness computer-based training.

Merger Agreement

On April 25, 2021, the Company entered into an Agreement and Plan of Merger (the “Merger Agreement”) with Proofpoint Holdings, LP (f/k/a Project Kafka Parent, LLC and Proofpoint Parent, LLC), a Delaware limited partnership (“Parent”), and Project Kafka Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Parent (“Merger Sub”), pursuant to which Merger Sub will merge with and into the Company (the “Merger” or the “Transaction”), with the Company surviving the Merger as a wholly owned subsidiary of Parent. Parent and Merger Sub are affiliates of funds advised by Thoma Bravo, L.P. (“Thoma Bravo”).

Pursuant to the terms of the Merger Agreement, at the effective time of the Merger (the “Effective Time”), each share of the Company’s common stock outstanding immediately prior to the effective time of the Merger (subject to certain exceptions, including shares of common stock owned by stockholders of the Company who did not vote in favor of the adoption of the Merger Agreement and properly exercised appraisal rights) will, at the Effective Time, automatically be converted into the right to receive $176.00 in cash, subject to applicable withholding taxes.

Completion of the Merger is subject to certain closing conditions, including (1) the approval of the Merger under applicable antitrust and foreign investment approvals, (2) the absence of any order, injunction or law prohibiting the Merger, (3) the accuracy of the other party’s representations and warranties, subject to certain materiality standards set forth in the Merger Agreement, (4) compliance in all material respects with the other party’s obligations under the Merger Agreement, and (5) no Company Material Adverse Effect (as defined in the Merger Agreement) having occurred since the date of the Merger Agreement. The parties expect the Transaction to close in the third quarter of 2021.

A special meeting of the Company’s stockholders to consider and vote on the proposal to adopt the Merger Agreement was held on July 23, 2021, and the stockholders approved the proposal to adopt the Merger Agreement.

Basis of Presentation and Consolidation

These condensed consolidated financial statements include the accounts of the Company and its wholly-owned subsidiaries. All intercompany transactions and balances have been eliminated in consolidation.

These condensed consolidated financial statements have been prepared in accordance with United States generally accepted accounting principles (“GAAP”), pursuant to the rules and regulations of the ~~Securities and Exchange Commission (the “~~SEC”). Certain information and note disclosures have been condensed or omitted pursuant to such rules and regulations. The accompanying Condensed Consolidated Balance Sheet as of December 31, 2020 is derived from audited financial statements as of that date but does not include all of the information and footnotes required by accounting principles generally accepted in the United States for complete financial statements. The unaudited condensed consolidated financial statements have been prepared on the same basis as the annual financial statements and, in the opinion of management, reflect all adjustments, which include only normal recurring adjustments, necessary for a fair statement of the periods presented. Certain prior period amounts have been adjusted due to adoption of Accounting Standards Update No. 2020-06, Debt-Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging-Contracts in Entity’s Own Equity (Subtopic 815-40) ~~(“ASU~~: ~~2020-06”).~~Accounting ~~Refer to Note 8 “Convertible Senior Notes”~~ for more information. The results of operations for the three months ended March 31, 2021 are not necessarily indicative of the results to be expected for the year ending December 31, 2021 or for other interim periods or for future years.

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Convertible Instruments and Contracts in an Entity’s Own Equity (“ASU 2020-06”). Refer to Note 8 “Convertible Senior Notes” for more information. The results of operations for the three and six months ended June 30, 2021 are not necessarily indicative of the results to be expected for the year ending December 31, 2021 or for other interim periods or for future years.

These condensed consolidated financial statements should be read in conjunction with the Company’s audited consolidated financial statements and accompanying notes for the year ended December 31, 2020 included in the Company’s Annual Report on Form 10-K filed with the SEC. The Company’s significant accounting policies are described in Note 1 to those audited consolidated financial statements.

Use of Estimates

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements, and the reported amounts of expenses during the reporting periods. Actual results could differ from those estimates and such difference may be material to the financial statements.

9Due to the Coronavirus (“COVID-19”) pandemic, there has been uncertainty and disruption in the global economy and financial markets. The Company is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities as of June 30, 2021. These estimates may change, as new events occur and additional information is obtained, as well as other factors related to COVID-19 that could result in material impacts to our consolidated financial statements in future reporting periods.

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date of the financial statements, and the reported amounts of expenses during the reporting period. Actual results could differ from those estimates and such difference may be material to the financial statements.

Due to the Coronavirus (“COVID-19”) pandemic, there has been uncertainty and disruption in the global economy and financial markets. The Company is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities as of March 31, 2021. These estimates may change, as new events occur and additional information is obtained, as well as other factors related to COVID-19 that could result in material impacts to our consolidated financial statements in future reporting periods.

Goodwill and Intangible Assets

Goodwill represents the excess of the purchase price of the acquired enterprise over the fair value of identifiable assets acquired and liabilities assumed. The Company performs an annual goodwill impairment test during the fourth quarter of a calendar year and more frequently if an event or circumstances indicates that impairment may have occurred. For the purposes of impairment testing, the Company has determined that it has one operating segment and one reporting unit. To test goodwill for impairment, the Company compares the reporting unit’s carrying value with its fair value. If the carrying value of the reporting unit exceeds the reporting unit’s fair value, then the impairment charge equal to the difference is recorded; however, the loss recognized would not exceed the total amount of goodwill allocated to the reporting unit. The identification and measurement of goodwill impairment involves the estimation of the fair value of the Company. No impairment indicators were identified by the Company as of ~~March~~June 3130, 2021.

Intangible assets consist of developed technology, customer relationships, trademarks and patents, and order backlog. The values assigned to intangibles are based on estimates and judgments regarding expectations for success and life cycle of solutions and technologies acquired.

Intangible assets are amortized on a straight-line basis over their estimated lives, which approximate the pattern in which the economic benefits of the intangible assets are consumed, as follows (in years):

	Low		High
Developed technology		2		7
Customer relationships		2		8
Trade names and trademarks		1		5
Patents		4		5
Order backlog		1		3

Comprehensive Loss

Comprehensive loss includes all changes in equity that are not the result of transactions with stockholders. The Company’s comprehensive loss consists of its net loss and changes in unrealized gains (losses) from its available-for-sale investments. The Company had no material reclassifications out of accumulated other comprehensive income into net loss for the three and six months ended ~~March~~June 3130, 2021 and 2020.

Accounting Pronouncements Adopted in 2021

In August 2020, the Financial Accounting Standards Board ("FASB") issued ASU No. 2020-06, which simplifies the accounting for certain financial instruments with characteristics of liabilities and equity, including convertible instruments and contracts in an entity’s own equity.

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The Company adopted ASU 2020-06 effective January 1, 2021 using the full retrospective transition method. Refer to Note 8 “Convertible Senior Notes” regarding the impact of adoption of ASU 2020-06 on the Company’s consolidated financial statements.

In December 2019, the FASB issued ASU No. 2019-12, Income Taxes (Topic 740): Simplifying the Accounting for Income Taxes (“ASU 2019-12”). ASU 2019-12 removes certain exceptions related to the approach for intraperiod tax allocation, the methodology for calculating income taxes in an interim period and the recognition of deferred tax liabilities for outside basis differences. ASU 2019-12 also amends other aspects of the guidance to help simplify and promote consistent application of GAAP. The Company adopted ASU 2019-12 effective January 1, 2021 prospectively. The adoption of ASU 2018-15 did not have a material impact on the Company’s condensed consolidated financial statements.

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2. Revenue, Deferred Revenue and Deferred Contract Costs

The core principle of ASC 606 is to recognize revenue to depict the transfer of services or products to customers in an amount that reflects the consideration the Company expects to be entitled to in exchange for those services or products. The Company applies significant judgment in identifying and evaluating any terms and conditions in contracts which may impact revenue recognition. The principle is achieved through the following five-step approach:

•

Identification of the contract, or contracts, with the customer - The Company considers the terms and conditions of the contract and its customary business practice in identifying its contracts under ASC 606. The Company determines it has a contract with a customer when the contract is approved, the Company can identify each party’s rights regarding the services and products to be transferred, the Company can identify the payment terms for the services and products, the Company has determined the customer has the ability and intent to pay and the contract has commercial substance. At contract inception, the Company evaluates whether two or more contracts should be combined and accounted for as a single contract and whether the combined contract or single contract includes more than one performance obligation. The Company applies judgment in determining the customer’s ability and intent to pay, which is based on a variety of factors, including the customer’s historical payment experience or, in the case of a new customer, credit and financial information pertaining to the customer.

•

Identification of the performance obligation in the contract - Performance obligations promised in a contract are identified based on the services or products that will be transferred to the customer that are both i) capable of being distinct, whereby the customer can benefit from the service or product either on its own or together with other resources that are readily available from third parties or from the Company, and ii) distinct in the context of the contract, whereby the transfer of the services or products is separately identifiable from other promises in the contract. To the extent a contract includes multiple promised services or products, the Company applies judgment to determine whether promised services or products are capable of being distinct and distinct in the context of the contract. If these criteria are not met the promised services or products are accounted for as a combined performance obligation.

•

Determination of the transaction price - The transaction price is determined based on the consideration to which the Company expects to be entitled in exchange for transferring services and products to the customer. Variable consideration is included in the transaction price if, in the Company’s judgment, it is probable that a significant future reversal of cumulative revenue under the contract will not occur. None of the Company’s contracts contain a significant financing component.

•

Allocation of the transaction price to the performance obligations in the contract - If the contract contains a single performance obligation, the entire transaction price is allocated to the single performance obligation. Contracts that contain multiple performance obligations require an allocation of the transaction price to each performance obligation based on a relative standalone selling price, or SSP, basis.

•

Recognition of revenue when, or as, the Company satisfies a performance obligation - The Company recognizes revenue when control of the services or products are transferred to the customers, in an amount that reflects the consideration the Company expects to be entitled to in exchange for those services or products. The Company records its revenue net of any value added or sales tax.

The Company generates sales directly through its sales team and, to a growing extent, through its channel partners. Sales to channel partners are made at a discount and revenues are recorded at this discounted price once all revenue recognition criteria are met. Channel partners generally receive an order from an end-customer prior to placing an order with the Company, and these partners do not carry any inventory of the Company’s products or solutions. Payment from channel partners is not contingent on the partner’s success in sales to end-customers. In the event that the Company offers rebates, joint marketing funds, or other incentive programs to a partner, recorded revenues are reduced by these amounts accordingly.

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Payment terms on invoiced amounts are typically 30 to 45 days.

Disaggregation of Revenue

The Company derives its revenue primarily from: (1) subscription service revenue; (2) subscription software revenue, and (3) hardware and services, which include professional service and training revenue provided to customers related to their use of the platform.

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The following table presents the Company’s revenue disaggregation:

	Three Months Ended March 31,
	Three Months Ended June 30,				Six Months Ended June 30,
	2021		2020		2021		2020
Subscription service revenue	$	~~270~~286,~~941~~705	$	~~236~~244,~~721~~137	$	557,646	$	480,858
Subscription software revenue		1216,~~671~~805		710,~~348~~755		29,476		18,103
Hardware and services		45,~~219~~143		53,~~705~~546		9,362		9,251
Total revenue	$	~~287~~308,~~831~~653	$	~~249~~258,~~774~~438	$	596,484	$	508,212

Subscription service revenue

Subscription service revenue is derived from a subscription-based enterprise licensing model with contract terms typically ranging from one to three years, and consists of (1) subscription fees from the licensing of the Company’s security-as-a-service platform and it’s various components, (2) subscription fees for software with support and related future updates where the software updates are critical to the customers’ ability to derive benefit from the software due to the fast changing nature of the technology. These function together as one performance obligation, and (3) subscription fees for the right to access the Company’s customer support services for software with significant standalone functionality, managed services and support services for hardware. The hosted on-demand service arrangements do not provide customers with the right to take possession of the software supporting the hosted services. Support revenue is derived from ongoing security updates, upgrades, bug fixes, and maintenance. A time-elapsed method is used to measure progress because the Company transfers control evenly over the contractual period. Accordingly, the fixed consideration related to subscription service revenue is generally recognized on a straight-line basis over the contract term beginning on the date access is provided, as long as other revenue recognition criteria have been met. Most of the Company’s contracts are non-cancelable over the contract term. Customers typically have the right to terminate their contract for cause if the Company fails to perform in accordance with the contractual terms. Some of the Company’s customers have the option to purchase additional subscription services at a stated price. These options are evaluated on a case-by-case basis but generally do not provide a material right as they are priced at or above the Company’s SSP and, as such, would not result in a separate performance obligation.

Subscription software revenue

Subscription software revenue is primarily derived from term-based software that is deployed on the customers’ own servers and has significant standalone functionality, is recognized upon transfer of control to the customer. The control for subscription software is transferred at the later of delivery to the customer or the software license start date.

Hardware and services

Hardware revenue consists of amounts derived from the sale of the Company’s on-premise hardware appliance, which is recognized upon passage of control, which occurs upon shipment of the product. Professional services revenue consists of fees associated with consulting, implementation and training services for assisting customers in implementing and expanding the use of the Company’s services and products. These services are distinct from subscription, subscription software licenses and hardware. Professional services do not result in significant customization of the Company’s services and products. The Company recognizes revenue related to the professional services as they are performed.

Contracts with multiple performance obligations

Most of the Company’s contracts with customers contain multiple performance obligations that are distinct and accounted for separately. The transaction price allocated to subscription services and subscription software that does not have significant standalone functionality is determined by considering factors such as historical pricing practices, and the selling price of hardware and professional services is estimated using a cost-plus model. The selling price for support of a functional subscription software license is calculated as a percentage of functional subscription software license value which is derived by analyzing internal pricing practice, customer expectations, and industry practice.

~~Variable consideration~~13

Revenue from sales is recorded at the net sales price, which is the transaction price, and includes estimates of variable consideration. The amount of variable consideration that is included in the transaction price is constrained, and is included in the net sales price only to the extent that it is probable that a significant reversal in the amount of the cumulative revenue will not occur when the uncertainty is resolved. If the Company’s services or products do not meet certain service level commitments, the Company’s customers are entitled to receive service credits representing a form of variable consideration. The Company has not historically experienced any significant incidents affecting the defined levels of

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~~reliability~~Variable and performance as required by the Company’s subscription contracts. Accordingly, any estimated refunds related to these contracts in the condensed consolidated financial statements are not material during the periods presented.consideration

Unbilled accounts receivables

Unbilled accounts receivable represents amounts for which the Company has recognized revenue, pursuant to its revenue recognition policy, for software licenses already delivered and professional services already performed, but billed in arrears and for which the Company believes it has an unconditional right to payment. The unbilled accounts receivable balance, included in accounts receivable in the condensed consolidated balance sheet, was $21,~~855~~584 and $1,963 as of ~~March~~June 3130, 2021 and December 31, 2020, respectively.

Deferred commissions

The Company capitalizes sales commissions and associated payroll taxes paid to internal sales personnel, and referral fees paid to independent third-parties, that are incremental to the acquisition of customer contracts. These costs are recorded as deferred commissions on the condensed consolidated balance sheets. The Company determines whether costs should be deferred based on its sales compensation plans, if the commissions are incremental and would not have occurred absent the customer contract. Sales commissions for renewal of a subscription contract are not considered commensurate with the commissions paid for the acquisition of the initial subscription contract given the substantive difference in commission rate between new and renewal contracts. Commissions paid upon the initial acquisition of a contract are amortized over an estimated period of benefit of five years while commissions paid related to renewal contracts are amortized over a contractual renewal period. Amortization is recognized based on the expected future revenue streams under the customer contracts. Amortization of deferred sales commissions is included in sales and marketing expense in the accompanying condensed consolidated statements of operations. The Company determines the period of benefit for commissions paid for the acquisition of the initial subscription contract by taking into consideration its initial estimated customer life and the technological life of the Company’s software and related significant features. The Company classifies deferred commissions as current or long-term based on the timing of when the Company expects to recognize the expense. The Company periodically reviews these deferred commission costs to determine whether events or changes in circumstances have occurred that could impact the period of benefit of these deferred contract acquisition costs. There were no material impairment losses recorded during the periods presented.

For the three months ended ~~March~~June 3130, 2021 and 2020, the Company capitalized $31,338 and $20,~~882~~783 of commission costs, respectively, and amortized $19,221 and $15,~~170~~370, respectively. For the six months ended June 30, 2021 and 2020, the Company capitalized $52,220 and $35,953 of commission costs, respectively, and amortized $1837,~~051~~272 and $1430,~~633~~003, respectively.

Deferred product costs

Deferred product costs are the incremental costs to fulfill a contract that are directly associated with each non-cancellable customer contract and primarily consist of royalty payments made to third parties, from whom the Company has obtained licenses to integrate certain software into its products. The deferred product costs are recognized based on the contractual term, and included in cost of revenue in the accompanying condensed consolidated statements of operations. The Company classifies deferred product costs as current or long-term based on the timing of when the Company expects to recognize the expense.

For the three months ended ~~March~~June 3130, 2021 and 2020, the Company capitalized $~~980~~1,038 and $~~1,176~~901 of deferred product costs, respectively, and amortized $1,~~021~~178 and $1,~~119~~035, respectively. For the six months ended June 30, 2021 and 2020, the Company capitalized $2,018 and $2,077 of deferred product costs, respectively, and amortized $2,199 and $2,154, respectively.

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Deferred revenue

The Company records deferred revenue when cash payments are received, or invoices are issued in advance of the Company’s performance, and generally recognizes revenue over the contractual term. The Company recognized $~~244~~256,~~876~~988 and $~~218~~222,~~622~~562 of revenue during the three months ended ~~March~~June 3130, 2021 and 2020, respectively, that was included in the deferred revenue balances at the beginning of the respective periods. The Company recognized $445,311 and $394,857 of revenue during the six months ended June 30, 2021 and 2020, respectively, that was included in the deferred revenue balances at the beginning of the respective periods.

Remaining performance obligations

Contracted revenue as of ~~March~~June 3130, 2021 that has not yet been recognized (“contracted not recognized”) was $~~807~~836,~~580~~335, which includes deferred revenue and non-cancellable amounts that will be invoiced and recognized as revenue in future periods and excludes contracts with an original expected length of one year or less. The Company expects 5960% of contracted and not recognized revenue to be recognized over the next twelve months, 3938% in years two and three, with the remaining balance recognized thereafter.

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3. Acquisitions

Acquisitions are accounted for under the purchase method of accounting in which the tangible and identifiable intangible assets and liabilities of each acquired company are recorded at their respective fair values as of each acquisition date, including an amount for goodwill representing the difference between the respective acquisition consideration and fair values of identifiable net assets. The Company believes that for the acquisitions described below, the combined entities will achieve savings in corporate overhead costs and opportunities for growth through expanded geographic and customer segment diversity with the ability to leverage additional products and capabilities. These factors, among others, contributed to purchase prices in excess of the estimated fair values of the acquired companies’ net identifiable assets acquired and, as a result, goodwill was recorded in connection with the acquisitions. Goodwill related to the acquisitions of InteliSecure, Inc. is not deductible for tax purposes. Goodwill related to the acquisition of The Defence Works Limited is deductible for tax purposes.

While the Company uses its best estimates and assumptions as part of the purchase price allocation process to value assets acquired and liabilities assumed at the acquisition date, these estimates and assumptions are subject to refinement. When additional information becomes available, such as finalization of negotiations of working capital adjustments and tax related matters, the Company may revise its preliminary purchase price allocation. As a result, during the preliminary purchase price allocation period, which may be up to one year from the acquisition date, the Company may record adjustments to the assets acquired and liabilities assumed, with the corresponding offset to goodwill. Subsequent to the purchase price allocation period, adjustments to assets acquired or liabilities assumed are recognized in the operating results.

2021 Acquisition

InteliSecure, Inc.

On March 2, 2021 (the “InteliSecure Acquisition Date”), pursuant to the terms of the merger agreement, the Company acquired all shares of InteliSecure, Inc. (“InteliSecure”), a data loss protection managed services company. With this acquisition, the Company expects to strengthen its cloud-based people-centric security platform by enhancing customers’ ability to protect critical data in diverse environments. This factor, among others, contributed to a purchase price in excess of the estimated fair value of acquired net identifiable assets and, as a result, goodwill was recorded in connection with the acquisition. The results of operations and the fair values of the acquired assets and liabilities assumed have been included in the accompanying condensed consolidated financial statements since the InteliSecure Acquisition Date.

At the InteliSecure Acquisition Date, the consideration transferred was $59,188, net of cash acquired of $1,612. Of the consideration transferred, $6,000 was held in escrow to secure indemnification obligations, and $3,750 was classified and recorded as contingent consideration on the condensed consolidated balance sheet as of the InteliSecure Acquisition Date.

The Company expects to pay the contingent consideration within a year of the balance sheet date depending on the timing and value of ~~contract~~contracts ~~assignments~~renewed following the InteliSecure Acquisition Date and the maximum potential payment amount could be up to $4,500. The fair value of the contingent consideration liability was determined using unobservable inputs as of the acquisition date. These inputs include the estimated amount and timing of future contract ~~assignments~~renewals, the probability of success and a risk-adjusted discount rate to adjust the probability-weighted cash flows to present value.

The Company incurred $1,454 in acquisition-related costs, which were recorded within operating expenses for the three months ended March 31, 2021. The revenue from InteliSecure was not material for the three months ended March 31, 2021, and due to the continued integration of the combined businesses, it was impractical to determine the earnings. Managed service revenue is presented as part of subscription revenue in the Company’s condensed consolidated statements of operations.15

The Discounted Cash Flow Method was used to value the acquired customer relationships and order backlog. The Cost to Recreate Method was used to value the acquired developed technology. Management applied significant judgment in estimating the fair values of these intangible assets, which involved the use of significant assumptions with respect to forecasted revenue, forecasted operating results and discount rates.

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The Company incurred $1,580 in acquisition-related costs, which were recorded within operating expenses for the six months ended June 30, 2021. The revenue from InteliSecure was not material for the three and six months ended June 30, 2021, and due to the continued integration of the combined businesses, it was impractical to determine the earnings. Managed service revenue is presented as part of subscription revenue in the Company’s condensed consolidated statements of operations.

The following table summarizes the fair values of tangible assets acquired, liabilities assumed, intangible assets and goodwill:

	Estimated Fair Value			Estimated Useful Life (in years)
Current assets	$	5,100		N/A
Fixed assets		765		N/A
Operating lease right-of-use asset		2,761		N/A
Other assets		155		N/A
Customer relationships		11,400			7
Order backlog		1,900			2
Core/developed technology		1,800			3
Operating lease liabilities		(2,704	)	N/A
Deferred revenue		(3,866	)	N/A
Deferred tax liabilities, net		(389	)	N/A
Other liabilities		(5,705	)	N/A
Goodwill		49,583		Indefinite
	$	60,800

2020 Acquisition

The Defence Works Limited

On May 5, 2020, the Company completed its acquisition of The Defence Works Limited. The acquisition brings a library of interactive content to the Company’s security awareness training portfolio and provides the Company’s customers innovative content to support their security education programs. The total consideration was $2,767, of which $766 was allocated to goodwill and $2,400 was allocated to intangible assets. The acquired intangible assets consist of content library which is included within the developed technology assets in Note 4 “Goodwill and Intangible Assets.”

Pro forma information has not been presented as the impact of these acquisitions, individually and in the aggregate, was not material to the Company’s condensed financial statements.

4. Goodwill and Intangible Assets

The goodwill activity and balances are presented below:

Balance as of December 31, 2020	$	688,454
Acquisition during the period		49,583
Purchase accounting adjustments		—
Balance as of March 31, 2021	$	738,037
Balance as of June 30, 2021	$	738,037

~~Intangible assets, excluding goodwill, consisted of the following:~~16

	March 31, 2021							December 31, 2020
	Gross Carrying Amount		Accumulated Amortization			Net Carrying Amount		Gross Carrying Amount		Accumulated Amortization			Net Carrying Amount
Developed technology	$	235,269	$	(162,178	)	$	73,091	$	233,469	$	(151,562	)	$	81,907
Customer relationships		98,600		(42,345	)		56,255		87,200		(38,896	)		48,304
Trade names and patents		1,330		(1,199	)		131		3,730		(3,549	)		181
Order backlog		1,900		(74	)		1,826		8,100		(8,100	)		—
	$	337,099	$	(205,796	)	$	131,303	$	332,499	$	(202,107	)	$	130,392

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~~Amortization~~Intangible ~~of intangible~~ assets ~~expense was $14~~,~~189~~ ~~and~~excluding ~~$14~~goodwill,~~451~~ ~~for~~consisted of the ~~three months ended March 31, 2021 and 2020, respectively.~~following:

Future estimated amortization of intangible assets expense as of March 31, 2021 are presented below:

	June 30, 2021							December 31, 2020
	Gross Carrying Amount		Accumulated Amortization			Net Carrying Amount		Gross Carrying Amount		Accumulated Amortization			Net Carrying Amount
Developed technology	$	235,269	$	(172,897	)	$	62,372	$	233,469	$	(151,562	)	$	81,907
Customer relationships		98,600		(46,074	)		52,526		87,200		(38,896	)		48,304
Trade names and patents		1,330		(1,249	)		81		3,730		(3,549	)		181
Order backlog		1,900		(312	)		1,588		8,100		(8,100	)		—
	$	337,099	$	(220,532	)	$	116,567	$	332,499	$	(202,107	)	$	130,392

Year ending December 31,
2021, remainder	$	42,765
2022		35,239
2023		24,887
2024		15,539
2025		7,667
2026		3,297
Thereafter		1,909
Total	$	131,303

Amortization of intangible assets expense was $14,736 and $13,939 for the three months ended June 30, 2021 and 2020, respectively, and $28,925 and $28,390 for the six months ended June 30, 2021 and 2020, respectively.

Future estimated amortization of intangible assets expense as of June 30, 2021 are presented below:

Year ending December 31,
2021, remainder	$	28,029
2022		35,239
2023		24,887
2024		15,539
2025		7,667
2026		3,297
Thereafter		1,909
Total	$	116,567

5. Fair Value Measurements and Investments

Fair Value Measurements

Fair value is defined as the price that would be received to sell an asset or paid to transfer a liability (i.e., the “exit price”) in an orderly transaction between market participants at the measurement date. A hierarchy for inputs used in measuring fair value has been defined to minimize the use of unobservable inputs by requiring the use of observable market data when available. Observable inputs are inputs that market participants would use in pricing the asset or liability based on active market data. Unobservable inputs are inputs that reflect the Company’s assumptions about the assumptions market participants would use in pricing the asset or liability based on the best information available in the circumstances.

The fair value hierarchy prioritizes the inputs into three broad levels:

•

Level 1: Quoted (unadjusted) prices in active markets for identical assets or liabilities. The Company’s Level 1 assets generally consist of money market funds.

•

Level 2: Observable inputs other than quoted prices included in Level 1, such as quoted prices for similar assets or liabilities in active markets; quoted prices for identical or similar assets or liabilities in markets that are not active; or other inputs that are observable or can be corroborated by observable market data for substantially the full term of the asset or liability. The Company’s Level 2 assets and liabilities generally consist of corporate debt securities, commercial papers, U.S. agency and Treasury securities and convertible senior notes.

• Level 3: Unobservable inputs to the valuation methodology that are supported by little or no market activity and that are significant to the measurement of the fair value of the assets or liabilities. Level 3 assets and liabilities include those whose fair value measurements are determined using pricing models, discounted cash flow methodologies or similar valuation techniques, as well as significant management judgment or estimation. The Company’s Level 3 liabilities generally consist of the contingent payment in connection with the acquisition of InteliSecure.

The following tables summarize, for each category of assets or liabilities carried at fair value, the respective fair value as of March 31, 2021 and December 31, 2020 and the classification by level of input within the fair value hierarchy:17

	March 31, 2021
	Total		Level 1		Level 2		Level 3
Assets
Cash equivalents:
Money market funds	$	842,328	$	842,328	$	—	$	—
Total financial assets	$	842,328	$	842,328	$	—	$	—
Liabilities
Acquisition-related contingent consideration	$	3,750	$	—	$	—	$	3,750

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The following tables summarize, for each category of assets or liabilities carried at fair value, the respective fair value as of June 30, 2021 and December 31, 2020 and the classification by level of input within the fair value hierarchy:

	June 30, 2021
	Total		Level 1		Level 2		Level 3
Assets
Cash equivalents:
Money market funds	$	890,965	$	890,965	$	—	$	—
Total financial assets	$	890,965	$	890,965	$	—	$	—
Liabilities
Acquisition-related contingent consideration	$	3,402	$	—	$	—	$	3,402

	December 31, 2020
	Total		Level 1		Level 2		Level 3
Assets
Cash equivalents:
Money market funds	$	865,924	$	865,924	$	—	$	—
Total financial assets	$	865,924	$	865,924	$	—	$	—

Based on quoted market prices as of ~~March~~June 3130, 2021 and December 31, 2020, the fair value of the 2024 Notes (Note 8) was approximately $~~998~~1,~~200~~156,541 and $1,021,200, respectively, determined using Level 2 inputs as they are not actively traded in markets.

The following table represents a reconciliation of the acquisition-related contingent consideration liability measured at fair value on a recurring basis, using significant unobservable inputs (Level 3):

	Three Months Ended March 31,
	Three Months Ended June 30,			Six months ended June 30,
	2021			2021
Beginning balance	$	—3,750		$	—
Additions during the period		~~3,750~~—			3,750
Payment during the period		—			—
Adjustments to fair value during the period recorded in general and administrative expenses		—(348	)		(348	)
Ending balance	$	3,~~750~~402		$	3,402

Investments

The cost and fair value of the Company’s cash and cash equivalents as of ~~March~~June 3130, 2021 and December 31, 2020 were as follows:

March 31, 2021

June 30, 2021

Amortized Cost

Unrealized Gains

Unrealized Losses

Fair Value

Cash and cash equivalents:

Cash

4038,~~222~~341

—

4038,~~222~~341

Money market funds

~~842~~890,~~328~~965

—

~~842~~890,~~328~~965

Total

~~882~~929,~~550~~306

—

~~882~~929,~~550~~306

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	December 31, 2020
	Amortized Cost		Unrealized Gains		Unrealized Losses		Fair Value
Cash and cash equivalents:
Cash	$	44,355	$	—	$	—	$	44,355
Money market funds		865,924		—		—		865,924
Total	$	910,279	$	—	$	—	$	910,279

The Company reviews its investments on a quarterly basis to identify and evaluate investments that have an indication of possible impairment and has determined that no other-than-temporary impairments were required to be recognized during the three and six months ended ~~March~~June 3130, 2021 and 2020.

6. Leases

The Company determines if an arrangement is, or contains, a lease at inception. Operating leases are included in operating right-of-use assets and operating lease liabilities in the condensed consolidated balance sheets. The Company does not separate non-lease components from lease components for its real estate and data center leases and instead account for each separate lease component, and non-lease components associated with that lease component, as a single lease component. The Company does not recognize right-of-use assets and lease liabilities for short-term leases, which have a lease term of twelve months or less.

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The Company does not recognize right-of-use assets and lease liabilities for short-term leases, which have a lease term of twelve months or less.

The Company has operating leases for corporate offices, research and development facilities, sales and marketing offices, and data centers. The Company’s real estate leases have remaining lease terms for up to ten years, some of which include options to extend the lease period up to ten years. The data center leases have remaining lease terms up to three years, some of which have renewal periods of one year.

The components of lease expense were as follows:

	Three Months Ended March 31,
	Three Months Ended June 30,				Six Months Ended June 30,
	2021		2020		2021		2020
Operating lease cost	$	10,~~331~~214	$	7,~~108~~203	$	20,545	$	14,311
Short-term lease cost		~~427~~487		~~674~~617		914		1,291
Variable lease cost		1,~~769~~920		1,~~038~~127		3,689		2,165
Total lease cost	$	12,~~527~~621	$	8,~~820~~947	$	25,148	$	17,767

Supplemental information related to leases was as follows:

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
	2021			2020			2021			2020
Cash paid for amounts included in the measurement of operating lease liabilities	$	76,~~088~~788		$	96,~~559~~408		$	13,876		$	15,967
Right-of-use assets obtained in exchange for operating lease obligations	$	84,~~311~~010		$	918,~~535~~660		$	12,321		$	28,195
Weighted-average remaining lease term - operating leases	~~9 years~~			~~5 years~~			9 years			5 years
Weighted-average discount rate - operating leases		~~4.64~~	%		~~5.00~~	%		4.59	%		4.32	%

~~Maturities of lease liabilities as of March 31, 2021 were as follows:~~19

	Operating Leases
Year ending December 31,
2021, remainder	$	20,422
2022		39,193
2023		28,751
2024		24,388
2025		23,717
2026		21,817
Thereafter		100,809
Total lease payments		259,097
Less imputed interest		(49,026	)
Total	$	210,071

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Maturities of lease liabilities as of June 30, 2021 were as follows:

	Operating Leases
Year ending December 31,
2021, remainder	$	15,351
2022		41,211
2023		30,316
2024		24,624
2025		23,812
2026		21,892
Thereafter		101,160
Total lease payments		258,366
Less imputed interest		(47,632	)
Total	$	210,734

7. Contingencies

Contingencies

Under the indemnification provisions of the Company’s customer agreements, the Company agrees to indemnify, ~~and~~ defend, and hold harmless its customers against, among other things, infringement of any patent, trademark or copyright under any country’s laws or the misappropriation of any trade secret arising from the customers’ legal use of the Company’s solutions. The exposure to the Company under these indemnification provisions is generally limited to the total amount paid by the customers under the applicable customer agreement. However, certain indemnification provisions potentially expose the Company to losses in excess of the aggregate amount paid to the Company by the customer under the applicable customer agreement. To date, there have been no claims against the Company or its customers pursuant to these indemnification provisions.

Legal Contingencies

From time to time, the Company may be involved in legal proceedings and subject to claims in the ordinary course of business. For lawsuits where the Company is the defendant, the Company is in the process of defending these litigation matters, and while there can be no assurances and the outcomes of these matters are currently not determinable, the Company currently believes that there are no existing claims or proceedings that are likely to have a material adverse effect on the Company’s financial position, results of operations or cash flows.

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matters, and while there can be no assurances and the outcomes of these matters are currently not determinable, the Company currently believes that there are no existing claims or proceedings that are likely to have a material adverse effect on the Company’s financial position, results of operations or cash flows.

8. Convertible Senior Notes

Effective January 1, 2021, the Company adopted ASU No. 2020-06 using the full retrospective method. Under this method, the Company is presenting the consolidated financial statements as of December 31, 2020, and for the three and six months ended ~~March~~June 3130, 2020, as if ASU 2020-06 had been effective for these periods beginning on January 1, 2020. ASU 2020-06 removed the liability and equity separation model for the Company’s Senior Convertible Notes. As a result, the Company no longer separately presents in stockholder’s equity the embedded conversion feature for its Senior Convertible Notes and accounts for the Notes as a single liability instrument. The embedded conversion feature is no longer being amortized as interest expense over the life of the 2024 Notes.

As of January 1, 2020, the Company recorded a $163,023 reduction to additional paid-in-capital to remove the equity component of the Senior Convertible Notes from its balance sheet and a $40,500 cumulative reduction to accumulated deficit related to non-cash debt discount amortization recognized in periods prior to the adoption of ASU 2020-06, which resulted in a corresponding reduction of $122,523 to the debt discount associated with the Senior Convertible Notes.

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Select condensed consolidated balance sheet line items, which reflect the adoption of the new guidance, are as follows:

	December 31, 2020
	As Previously Reported			Adjustments			As Adjusted
Liabilities and Stockholders’ Equity
Convertible senior notes	$	783,561		$	122,523		$	906,084
Total liabilities	$	2,056,966		$	122,523		$	2,179,489
Stockholders’ equity
Additional paid-in capital	$	1,470,497		$	(163,023	)	$	1,307,474
Accumulated deficit	$	(889,403	)	$	40,500		$	(848,903	)
Total stockholders’ equity	$	441,744		$	(122,523	)	$	319,221

Select unaudited condensed consolidated statements of operations line items, which reflect the adoption of the new guidance, are as follows:

	Three Months Ended March 31, 2020
	Three Months Ended June 30, 2020
	As Previously Reported			Adjustments		As Adjusted
Operating loss	$	(4110,~~769~~830	)	$	—	$	(4110,~~769~~830	)
Interest expense	$	(89,~~920~~013	)	$	7,~~396~~488	$	(1,~~524~~525	)
Net loss	$	(7422,~~237~~595	)	$	7,~~396~~488	$	(6615,~~841~~107	)
Net loss per share, basic and diluted	$	(10.3039	)	$	0.13	$	(10.1726	)
	Six Months Ended June 30, 2020
	As Previously Reported			Adjustments		As Adjusted
Operating loss	$	(52,599	)	$	—	$	(52,599	)
Interest expense	$	(17,933	)	$	14,884	$	(3,049	)
Net loss	$	(96,832	)	$	14,884	$	(81,948	)
Net loss per share, basic and diluted	$	(1.69	)	$	0.26	$	(1.43	)

Select unaudited condensed consolidated statement of cash flows line items, which reflect the adoption of the new guidance are as follows:

Three Months Ended March 31, 2020

Six Months Ended June 30, 2020

As Previously Reported

Adjustments

As Adjusted

Cash flows from operating activities

Net loss

(7496,~~237~~832

)

714,~~396~~884

(6681,~~841~~948

)

Adjustments to reconcile net loss to net cash provided by operating activities:

Amortization of debt issuance costs and accretion of debt discount

816,~~345~~783

(714,~~396~~884

)

~~949~~1,899

Net cash provided by operating activities

92122,~~174~~784

—

92122,~~174~~784

0.25% Convertible Senior Notes due 2024

On August 23, 2019, the Company issued $~~920,000 aggregate principal amount of 0.25% Convertible Senior Notes due 2024 (the “2024 Notes”). The offering represented $800,000 aggregate principal amount of the 2024 Notes plus the full~~

1921

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920,000 aggregate principal amount of 0.25% Convertible Senior Notes due 2024 (the “2024 Notes”). The offering represented $800,000 aggregate principal amount of the 2024 Notes plus the full exercise of the initial buyers’ option to purchase up to an additional $120,000 aggregate principal amount. The net proceeds after the agent’s discount and issuance costs of $19,065 from the 2024 Notes offering were approximately $900,935. The Company used $84,871 of the net proceeds from the offering to pay the cost of the capped call transactions described below. The Company expects to use the remaining net proceeds for general corporate purposes, which may include acquisitions or other strategic transactions. The 2024 Notes are senior unsecured, unsubordinated obligations of the Company. The 2024 Notes bear interest at 0.25% per year, payable semi-annually in arrears every February 15 and August 15, beginning on February 15, 2020. The 2024 Notes mature on August 15, 2024, unless repurchased, redeemed or converted in accordance with their terms prior to such date.

The initial conversion rate is 6.4941 shares of the Company’s common stock per $1 principal amount of the 2024 Notes, which equates to an initial conversion price of $153.99 per share of common stock. Throughout the term of the 2024 Notes, the conversion rate may be adjusted upon the occurrence of certain events.

At the Company’s option, on or after August 20, 2022, the Company will be able to redeem all or a portion of the 2024 Notes at 100% of the principal amount, plus any accrued and unpaid interest, under certain conditions. The Company may redeem the 2024 Notes in shares of the Company’s common stock, cash, or some combination of each.

Prior to April 15, 2024, the 2024 Notes will be convertible at the option of the holders only upon the satisfaction of certain conditions and during certain periods upon the following circumstances:

•

during any calendar quarter commencing after December 31, 2019, if the last reported sale price of the Company’s common stock for at least 20 trading days (whether or not consecutive) during the period of 30 consecutive trading days ending on, and including, the last trading day of the preceding calendar quarter is greater than or equal to 130% of the applicable conversion price on each such trading day;

•

during the five business day period after any five consecutive trading day period in which the trading price per $1 principal amount of the 2024 Notes for each trading day of that five day consecutive trading day period was less than 98% of the product of the last reported sale price of the Company’s common stock and the applicable conversion rate on each such trading day;

•

upon a notice of redemption in which case, the Company will increase the conversion rate for the 2024 Notes so surrendered for conversion in connection with such redemption notice in accordance with the indenture; or

•

upon the occurrence of specified corporate transactions, as described in the indenture.

On or after April 15, 2024, holders may convert their 2024 Notes at the applicable conversion rate at any time prior to the close of business on the second scheduled trading day immediately preceding the maturity date.

Holders of the 2024 Notes also have the right to require the Company to repurchase all or a portion of the 2024 Notes at 100% of the principal amount, plus accrued and unpaid interest, if any, upon the occurrence of certain fundamental changes to the Company.

The following table represents the carrying value of the 2024 Notes as of ~~March~~June 3130, 2021 and December 31, 2020:

	March 31, 2021			December 31, 2020
	June 30, 2021			December 31, 2020
Liability component:
Principal	$	920,000		$	920,000
Less: debt discount and issuance costs, net of amortization		(12,~~963~~009	)		(13,916	)
Net carrying amount	$	907,~~037~~991		$	906,084

Capped Calls

In connection with the issuance of the 2024 Notes, including the initial purchasers’ exercise of the option to purchase additional 2024 Notes, the Company entered into privately negotiated capped call transactions with certain counterparties (the “Capped Calls”). The Capped Calls are expected to reduce potential dilution to the Company’s common stock upon conversion of the 2024 Notes and/or offset any cash payments that the Company is required to make in excess of the principal amount of the converted 2024 Notes, as the case may be, with such reduction and/or offset subject to a cap. The Capped Calls have a cap price equal to $223.98 per share, subject to certain adjustments, and expire on August 15, 2024. The Capped Calls are subject to adjustment upon the occurrence of specified extraordinary events affecting the Company, including merger events, tender offers and announcement events. In addition, the Capped Calls are subject to certain specified additional disruption events that may give rise to a termination of the Capped Calls, including nationalization, insolvency or delisting, changes in law, failures to deliver, insolvency filings and hedging disruptions.

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For accounting purposes, the Capped Calls are separate transactions, and not part of the terms of the 2024 Notes. As these transactions meet certain accounting criteria, the Capped Calls are recorded in stockholders’ equity and are not accounted for as derivatives. The premium paid for the purchase of the Capped Calls in the amount of $83,720 and related issuance cost of $1,151 have been recorded as a reduction to additional paid-in capital and will not be remeasured.

~~For the three months ended March 31, 2021 and 2020, the effective interest rate was 0.67% and the Company incurred the following expenses related to the 2024 Notes:~~22

	Three Months Ended March 31,
	2021		2020
Interest expense related to contractual interest coupon	$	575	$	575
Amortization of debt discount and issuance costs		953		949
Total	$	1,528	$	1,524

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For the three and six months ended June 30, 2021 and 2020, the effective interest rate was 0.67% and the Company incurred the following expenses related to the 2024 Notes:

	Three Months Ended June 30,				Six Months Ended June 30,
	2021		2020		2021		2020
Interest expense related to contractual interest coupon	$	575	$	575	$	1,150	$	1,150
Amortization of debt discount and issuance costs		954		950		1,907		1,899
Total	$	1,529	$	1,525	$	3,057	$	3,049

9. Stockholder’s Equity

Stock-Based Compensation Plans

On March 30, 2012, the ~~Company’s board of directors (the “~~Board of Directors” ~~or the “Board”)~~ and the Company’s stockholders approved the 2012 Equity Incentive Plan (the “2012 Plan”), which became effective in April 2012. The 2012 Plan was amended, effective June 2019, when the Company’s stockholders approved an Amended and Restated 2012 Equity Incentive Plan (the “Amended 2012 Plan”) at the annual meeting of the stockholders on June 6, 2019. The Company has nine equity incentive plans: the Company’s 2002 stock option plan (the “2002 Plan”), the Amended 2012 Plan and seven plans assumed by the Company upon various business acquisitions. The assumed plans are the Cloudmark plan, the WebLife plan, the Meta Networks plan, the ObserveIT plan, the InteliSecure plan and two FireLayers plans. Upon the Company’s initial public offering, all shares that were reserved under the 2002 Plan but not issued, and shares issued but subsequently returned to the plan through forfeitures, cancellations and repurchases became part of the 2012 Plan and no further shares will be granted pursuant to the 2002 Plan. No further shares will be granted pursuant to the assumed plans. All outstanding stock awards under the 2002 Plan, the assumed plans and Amended 2012 Plan will continue to be governed by their existing terms. Under the Amended 2012 Plan, the Company has the ability to issue incentive stock options (“ISOs”), nonstatutory stock options (“NSOs”), restricted stock awards, stock bonus awards, stock appreciation rights (“SARs”), restricted stock units (“RSUs”), and performance stock units (“PSUs”). The Amended 2012 Plan also allows direct issuance of common stock to employees, outside directors and consultants at prices equal to the fair market value at the date of grant of options or issuance of common stock. Additionally, the Amended 2012 Plan provides for the grant of performance cash awards to employees, directors and consultants. The Company has the right to repurchase any unvested shares (at the option exercise price) of common stock issued directly or under option exercises. The right of repurchase generally expires over the vesting period.

Stock bonus and other liability awards are accounted for as liability-classified awards, because the obligations are based predominantly on fixed monetary amounts that are generally known at the inception of the obligation, to be settled with a variable number of shares of the Company’s common stock.

Under the equity incentive plans, the term of an option grant shall not exceed ten years from the date of its grant and options generally vest over a three to four-year period, with vesting on a monthly or annual interval. As of ~~March~~June 3130, 2021, 5,~~117~~190 shares were available for future grant. Restricted stock awards generally vest over a three to five-year period.

The Company net-share settles equity awards held by employees by withholding shares upon vesting to satisfy tax withholding obligations. The shares withheld to satisfy employee tax withholding obligations are returned to the Company’s Amended 2012 Plan and will be available for future issuance. Payments for employee’s tax obligations to the tax authorities are recognized as a reduction to additional paid-in capital and reflected as financing activities in the Company’s consolidated statements of cash flows.

Stock Options

There were no options granted during the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020.

The Company realized no income tax benefit from stock option exercises in each of the periods presented due to recurring losses and the valuation allowances for deferred tax assets.

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Stock option activity under the Plan was as follows:

	Shares Subject to Options Outstanding
	Number of Shares			Weighted Average Exercise Price		Weighted Average Remaining Contractual Term (in years)		Aggregate Intrinsic Value
Balance at December 31, 2020		821		$	33.25		3.56	$	84,699
Options exercised		(55132	)		1411.0284
Options forfeited and expired		(4	)		19.26
Balance at March 31, 2021		762		$	34.71		3.37	$	69,381
Balance at June 30, 2021		685		$	37.46		3.31	$	93,305

The total intrinsic value of options exercised was $618,~~424~~872 and $710,~~936~~067 for the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, respectively. Total cash proceeds from such option exercises were $1,563 and $3,522 for the six months ended June 30, 2021 and 2020, respectively.

The fair value of option grants that vested was $1,~~068~~904 and $21,~~965~~285 for the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, respectively.

As of ~~March~~June 3130, 2021, the Company had unamortized stock-based compensation expense of $21,~~416~~776 related to stock options that will be recognized over the average remaining vesting term of the options of 1.3116 years.

Restricted Stock and Performance Stock Units

A following table summarizes the activity of RSUs and PSUs:

	RSUs and PSUs Outstanding
	Number of Shares			Granted Fair Value Per Unit
Awarded and unvested at December 31, 2020		4,382		$	105.2120
Awards assumed per business acquisition		77			122.03
Awards granted		12,~~782~~007			~~126~~132.8904
Awards vested		(~~529~~772	)		~~107~~108.7067
Awards forfeited		(~~122~~353	)		~~110~~107.6606
Awarded and unvested at March 31, 2021		5,590		$	112.00
Awarded and unvested at June 30, 2021		5,341		$	114.90

As of ~~March~~June 3130, 2021, there was $~~441~~417,~~015~~972 of unamortized stock-based compensation expense related to unvested RSUs, which is expected to be recognized over a weighted average period of 3.6941 years.

The Company granted 348 shares of PSUs in the ~~three~~six months ended ~~March~~June 3130, 2021. The Company granted ~~152~~155 shares of PSUs and 11 restricted performance-based shares in the ~~three~~six months ended ~~March~~June 3130, 2020. The PSU and restricted shares vesting conditions were based on individual performance targets. Unamortized stock-based compensation expense was $4033,~~263~~536 as of ~~March~~June 3130, 2021.

Stock Bonus Awards and Other Liability Awards

The total accrued liability for the stock bonus awards and other liability awards was $38,~~957~~240 and $12,480 as of ~~March~~June 3130, 2021 and December 31, 2020, respectively.

During the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, 103 and 125 shares, respectively, of common stock earned under the stock bonus program were issued. Stock-based compensation expense related to stock bonus program was $38,~~957~~240 and $38,~~763~~200 for the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, respectively.

Employee Stock Purchase Plan

On March 30, 2012, the Board of Directors and the Company’s stockholders approved the 2012 Employee Stock Purchase Plan (the “ESPP”), which became effective in April 2012. A total of 745 shares of the Company’s common stock were initially reserved for future issuance under the ESPP. The number of shares reserved for issuance under the ESPP increased automatically on January 1 of each of the first eight years commencing with 2013 by the number of shares equal to 1% of the Company’s shares outstanding on the immediately preceding December 31, but not to exceed 1,490 shares, unless the Board of Directors, in its discretion, determines to make a smaller increase. As of March 31, 2021, there were 2,410 shares of the Company’s common stock available for future issuance under the ESPP.

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Asthe Board of ~~March 31~~Directors, ~~2021,~~in ~~the~~its ~~Company~~discretion, ~~expects~~determines to ~~recognize~~make ~~$1,336~~a ofsmaller ~~the~~increase. ~~total~~As ~~unamortized~~of ~~compensation~~June ~~cost~~30, ~~related~~2021, tothere ~~employee~~were ~~purchases~~2,205 ~~under~~shares of the ~~ESPP~~Company’s ~~over~~common astock ~~weighted~~available ~~average~~for ~~period~~future ofissuance ~~0.13~~under ~~years~~the ESPP.

The Company suspended its ESPP program after the ESPP purchase on May 14, 2021.

Restricted Stock and Deferred Shares

As part of the WebLife acquisition in 2017, 107 shares were deferred for certain key employees with the total fair value of $9,652, and a vesting period between three and four years. The Company recognized $2,~~920~~947 and $~~602~~1,204 of stock-based compensation in the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, respectively. As of ~~March~~June 3130, 2021, there was $8154 of unamortized stock-based compensation expense related to the unvested deferred shares. The deferred shares are subject to forfeiture if employment terminates prior to the lapse of the deferral date and are expensed over the vesting period.

As part of the acquisition of Wombat Security Technologies, Inc. in 2018, 51 shares were deferred for certain key employees with the total fair value of $5,458, and a vesting period of two years. The Company recognized $382 of stock-based compensation in the three months ended March 31, 2020. As of March 31, 2020, all shares were fully vested.

As part of the Meta Networks acquisition in 2019, 72 shares were deferred for certain key employees with the total fair value of $8,338 allocated to post-combination expense, and a vesting period of three years. The Company recognized $~~684~~1,376 and $~~692~~1,383 of stock-based compensation in the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, respectively. As of ~~March~~June 3130, 2021, there was $32,~~124~~432 of unamortized stock-based compensation expense related to the unvested deferred shares. The deferred shares are subject to forfeiture if employment terminates prior to the lapse of the deferral date and are expensed over the vesting period. They are considered issued and outstanding shares of the Company at the acquisition date and have the same rights as other shares of common stock.

Share Repurchase Program

On August 27, 2020, the Board of Directors approved a share repurchase program under which the Company is authorized to repurchase up to $300,000 of the Company’s common stock (the “Repurchase Program”). Repurchases under the Repurchase Program may be made through open market purchases (including through trading plans administered under pre-determined purchasing criteria), block trades and/or privately negotiated transactions, subject to market conditions, applicable legal requirements, and other relevant factors. The timing, volume and nature of the repurchases are at the discretion of management, based on its evaluation of the capital needs of the Company, market conditions, applicable legal requirements and other factors. The Repurchase Program does not have an expiration date and may be suspended or discontinued by the Company at any time without prior notice.

During the three months ended ~~March~~June 3130, 2021, the Company repurchased ~~209~~136 shares of common stock under the Repurchase Program in open market transactions at an average price of $~~124~~131.8765 per share, for an aggregate purchase price of $2617,~~087~~866. AsThe ofRepurchase ~~March~~Program ~~31,~~was ~~2021,~~suspended ~~$134,557~~in ~~remained~~April ~~available~~2021 ~~for~~when ~~future~~the ~~share~~Company ~~repurchases~~entered ~~under~~into the ~~Repurchase~~Merger ~~Program~~Agreement.

10. Net Loss per Share

Basic net loss per share of common stock is calculated by dividing the net loss by the weighted‑average number of shares of common stock outstanding for the period. The weighted‑average number of shares of common stock used to calculate basic net loss per share of common stock excludes those shares subject to repurchase related to stock options or restricted stock that were exercised or issued prior to vesting as these shares are not deemed to be issued for accounting purposes until they vest. Diluted net loss per share of common stock is computed by dividing the net loss using the weighted‑average number of shares of common stock, excluding common stock subject to repurchase, and, if dilutive, potential shares of common stock outstanding during the period. Basic and diluted net loss per common share was the same for all periods presented as the impact of all potentially dilutive securities outstanding was anti-dilutive.

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The following table presents the potentially dilutive common shares outstanding that were excluded from the computation of diluted net loss per share for the periods presented because including them would have been anti-dilutive:

	March 31, 2021		March 31, 2020
	June 30, 2021		June 30, 2020
Stock options to purchase common stock		~~762~~685		~~954~~930
Restricted stock units		5,~~590~~341		54,~~091~~982
Employee stock purchase plan		~~214~~—		~~157~~127
Common stock subject to repurchase		6437		~~156~~143
Bonus and other liability awards		3147		3274
2024 Notes		5,975		5,975
Total		12,~~636~~085		12,~~365~~231

11. Segment Reporting

Operating segments are reported in a manner consistent with the internal reporting supported and defined by the components of an enterprise about which separate financial information is available, provided and is evaluated regularly by the chief operating decision maker in deciding how to allocate resources and in assessing performance. The Company’s chief operating decision maker is its Chief Executive Officer. The Company’s Chief Executive Officer reviews financial information presented on a consolidated basis. The Company has one business activity, and there are no segment managers who are held accountable for operations, operating results and plans for levels or components below the consolidated unit level. Accordingly, the Company determined that it has one operating and reportable segment.

The following sets forth total revenue by geographic area. Revenue by geographic area is based upon the billing address of the customer:

	Three Months Ended March 31,
	Three Months Ended June 30,				Six Months Ended June 30,
	2021		2020		2021		2020
Total revenue:
United States	$	~~222~~242,~~630~~566	$	~~198~~205,~~625~~077	$	465,196	$	403,702
Rest of world		6566,~~201~~087		5153,~~149~~361		131,288		104,510
Total revenue	$	~~287~~308,~~831~~653	$	~~249~~258,~~774~~438	$	596,484	$	508,212

Long-lived tangible assets by geographic area are presented below:

	March 31, 2021		December 31, 2020
	June 30, 2021		December 31, 2020
Long-lived assets:
United States	$	9391,~~117~~320	$	96,356
Rest of world		1415,~~575~~806		14,674
Total long-lived assets	$	107,~~692~~126	$	111,030

12. Income Taxes

The Company’s quarterly provision for income taxes is based on an estimated effective annual income tax rate. The Company’s quarterly provision for income taxes also includes the tax impact of certain unusual or infrequently occurring items, if any, including changes in judgment about valuation allowances and effects of changes in tax laws or rates, in the interim period in which they occur.

Income tax expense for the three and six months ended ~~March~~June 3130, 2021 was $2,~~094~~312 and $4,406 on pre-tax losses of $4350,~~225~~603 and $93,828, respectively. The Company recognized income tax expense of $281,~~169~~660 and $29,829 on pre-tax losses of $3813,~~672~~447 and $52,119, for the three and six months ended ~~March~~June 3130, 2020, respectively. The income tax rate for the three and six months ended ~~March~~June 3130, 2021 varied from the United States statutory income tax rate primarily due to valuation allowances in the United States whereby pre-tax losses and income do not result in the recognition of corresponding income tax benefits and expenses. The income tax rate for the three and six months ended ~~March~~June 3130, 2020 varied from the United States statutory income tax rate primarily due to valuation allowances in the United States whereby pre-tax losses and income do not result in the recognition of corresponding income tax benefits and expenses and also due to the recognition of a $2627,~~989~~107 tax expense related to the transfer of certain intellectual property rights from the Company’s wholly owned subsidiary in Israel to the United States. which occurred in the quarter ended March 31, 2020.

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The Company’s effective tax rate for the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020 was negative 5% and negative 7357%, respectively.

The Company reviews the likelihood that it will realize the benefit of its deferred tax assets and, therefore, the need for valuation allowances, on a quarterly basis. There is no corresponding income tax benefit recognized with respect to losses incurred and no corresponding income tax expense recognized with respect to earnings generated in jurisdictions with a valuation allowance. This causes variability in the Company’s effective tax rate. The Company intends to maintain the valuation allowances until it is more likely than not that the net deferred tax assets will be realized.

As of ~~March~~June 3130, 2021, the Company’s gross uncertain tax benefits totaled $5456,~~901~~752, excluding related accrued interest and penalties of $2,~~225~~604. As of ~~March~~June 3130, 2021, $3435,~~104~~259 of the Company’s uncertain tax benefits, including related accrued interest and penalties, would impact the effective tax rate if recognized. During the ~~three~~six months ended ~~March~~June 3130, 2021, the Company’s gross uncertain tax benefits ~~decreased~~increased $~~132~~1,719. The ~~decrease~~increase is comprised of a $12,~~206~~149 ~~decrease~~increase for tax positions taken in ~~prior~~the ~~periods~~current period, offset by a $~~1,074~~430 ~~increase~~decrease for tax positions taken in ~~the~~prior ~~current period~~periods.

The Company is currently under audit by the Israel Tax Authority for tax years 2016 through 2018. Due to the audit by the Israel Tax Authority it is reasonably possible that the Company’s uncertain tax positions could change within the next 12 months. An estimate of the range of any change cannot be made. The Company believes it has recorded all appropriate provisions for all jurisdictions and open years. However, the Company can give no assurance that taxing authorities will not propose adjustments that would increase its tax liabilities. The Company is not currently under audit by the IRS or any similar taxing authority in any other material jurisdiction.

The Coronavirus Aid, Relief, and Economic Security Act (the “CARES Act”) was enacted by the United States on March 27, 2020. The CARES Act did not have a material impact on the Company’s provision for income taxes for the ~~three~~six months ended ~~March~~June 3130, 2021.

13. Defined Contribution Plan

The Company’s tax-deferred savings plan is qualified under Section 401(k) of the United States Internal Revenue Code. Employees may make voluntary, tax-deferred contributions to the 401(k) Plan up to the statutorily prescribed annual limit. The Company makes discretionary matching contributions to the 401(k) Plan on behalf of employees up to the limit determined by the Board of Directors. The Company contributed $1746 and $579,~~964~~ respectively, to the 401(k) Plan during the three months ended June 30, 2021 and 2020. The Company contributed $12,~~649~~710 and $2,228, respectively, to the 401(k) Plan during the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020.

~~14. Subsequent Event~~27

On April 25, 2021, the Company entered into the Merger Agreement with Parent and Merger Sub, providing for the Company’s acquisition by affiliates of funds advised by private equity investment firm Thoma Bravo, L.P.

As a result of the Merger, each share of the Company’s common stock outstanding immediately prior to the effective time of the Merger (the “Effective Time”) (subject to certain exceptions, including shares of common stock owned by stockholders of the Company who have not voted in favor of the adoption of the Merger Agreement and have properly exercised appraisal rights in accordance with Section 262 of the General Corporation Law of the State of Delaware) will, at the Effective Time, automatically be converted into the right to receive $176.00 in cash, subject to applicable withholding taxes.

Completion of the Merger is subject to certain closing conditions, including (1) the adoption of the Merger Agreement by a majority of the holders of the outstanding shares of common stock, (2) the expiration or early termination of the applicable waiting period under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended, and the approval of the Merger under other applicable antitrust and foreign investment approvals, (3) the absence of any order, injunction or law prohibiting the Merger, (4) the accuracy of the other party’s representations and warranties, subject to certain materiality standards set forth in the Merger Agreement, (5) compliance in all material respects with the other party’s obligations under the Merger Agreement, and (6) no Company Material Adverse Effect (as defined in the Merger Agreement) having occurred since the date of the Merger Agreement. The parties expect the transaction to close in the third quarter of 2021.

Until 11:59 p.m. (Eastern time) on June 9, 2021 (referred to as the “go-shop” period), the Company has the right to, among other things, (1) solicit alternative acquisition proposals, (2) provide information (including nonpublic information) to third parties in connection therewith pursuant to an acceptable confidentiality agreement, and (3) initiate or continue discussions with third parties in connection therewith. From and after June 9, 2021, the Company must comply with

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customary non-solicitation restrictions. Subject to certain customary “fiduciary out” exceptions, the Board is required to recommend that the Company’s stockholders adopt the Merger Agreement.

If the Merger Agreement is terminated in certain other circumstances, including by the Company in order to enter into a superior proposal or by Parent because the Board withdraws its recommendation in favor of the Merger, the Company would be required to pay Parent a termination fee of $368,900; provided that a lower fee of $122,980 will apply with respect to a termination to enter into a superior proposal during the “go-shop” period.

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ITEM 2. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS.

The following discussion and analysis of our financial condition and results of operations should be read in conjunction with the (1) unaudited condensed consolidated financial statements and the related notes thereto included elsewhere in this Quarterly Report on Form 10-Q, and (2) the audited consolidated financial statements and notes thereto and management’s discussion and analysis of financial condition and results of operations for the year ended December 31, 2020 included in our 2020 Annual Report on Form 10-K. This Quarterly Report on Form 10-Q contains “forward-looking statements” within the meaning of Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). These statements are often identified by the use of words such as “may,” “will,” “expect,” “believe,” “anticipate,” “intend,” “could,” “estimate,” or “continue,” and similar expressions or variations. Such forward-looking statements are subject to risks and uncertainties, including risk and uncertainty around our pending acquisition by Thoma Bravo, L.P., our expectations regarding the timing of the Transaction, the impact of the COVID-19 outbreak, and other factors that could cause actual results and the timing of certain events to differ materially from future results expressed or implied by such forward-looking statements. Factors that could cause or contribute to such differences include, but are not limited to, those identified herein, and those discussed in the section titled “Risk Factors,” set forth in Part II, Item 1A of this Form 10-Q and in our other SEC filings, including our 2020 Annual Report on Form 10-K. We disclaim any obligation to update any forward-looking statements to reflect events or circumstances after the date of such statements.

Pending Transaction

On April 25, 2021 we entered into the Merger Agreement, providing for the Transaction and our acquisition by affiliates of funds advised by private equity investment firm Thoma Bravo in an all-cash transaction valued at $12.3 billion. If the Transaction is completed, our stockholders will be entitled to receive $176.00 in cash for each share of our common stock they hold as of the ~~effective~~Effective ~~time~~Time of the Transaction. The Transaction is expected to close in the third quarter of 2021, subject to ~~approval by our stockholders and~~ regulatory authorities and the satisfaction of customary closing conditions. See Note 141 “~~Subsequent~~The ~~Event~~Company and Summary of Significant Accounting Policies ” to our condensed consolidated financial statements in this Quarterly Report on Form 10-Q for information regarding the Transaction.

Overview

Proofpoint is a leading next generation cybersecurity company that enables large and mid-sized organizations worldwide to protect their employees from advanced threats and compliance risks. Our security and compliance platform is comprised of an integrated suite of advanced threat protection, information protection, and brand protection solutions. These capabilities include email protection and authentication, advanced threat protection, data loss prevention, email encryption, SaaS application protection, response orchestration and automation, digital risk, security training, web browser isolation, archiving, eDiscovery, supervision, and secure communication. Our solutions are built on a flexible, cloud-based platform and leverage a number of proprietary technologies - including big data analytics, machine learning, deep content inspection, secure storage, advanced encryption, intelligent message routing, dynamic malware analysis, threat correlation, and virtual execution environments to address today’s rapidly changing threat and compliance landscape.

Our platform addresses this growing challenge by not only protecting data as it flows into and out of the enterprise via on-premises and cloud-based email, social media and other cloud applications, but also by keeping track of this information as it is modified and distributed throughout the enterprise for compliance and data loss prevention, and securely archiving these communications for compliance and discovery. We help organizations reduce their critical risk in five major ways:

•

Protecting users from the advanced attacks that target them via email, web, networks, social media, and cloud apps;

•

Preventing the theft or inadvertent loss of sensitive information and, in turn, ensuring compliance with regulatory data protection mandates;

•

Improving the resilience of end-users to the threats that target them and training them to be better caretakers of their organizations’ critical data;

•

Collecting, retaining, supervising and discovering communications and sensitive data for compliance and litigation support; and

•

Enabling organizations to respond quickly to security issues, providing both the intelligence and the context to prioritize incidents and orchestrate remediation actions.

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Our platform and its associated solutions are sold to customers on a subscription basis and can be deployed through our unique cloud-based architecture that leverages both our global data centers as well as optional points-of-presence behind our customers’ firewalls. Our flexible deployment model enables us to deliver superior security and compliance while maintaining the favorable economics afforded by cloud computing, creating a competitive advantage for us over legacy on-premises and cloud-only offerings.

We were founded in 2002 to provide a unified solution to help enterprises address their growing data security requirements. Our first solution was commercially released in 2003 to combat the burgeoning problem of spam and viruses and their impact on corporate email systems. To address the evolving threat landscape and the adoption of communication and collaboration systems beyond corporate email and networks, we have broadened our solutions to defend against a wide range of threats, including email, mobile apps and social media, to protect the information people create from both compromise and compliance risks, and to archive and govern corporate information. As the threat environment has continued to evolve, we have dedicated significant resources to meet the ongoing challenges that this highly dynamic environment creates for our customers such as investing significantly to expand the breadth of our data protection platform as these expenditures are primarily in connection with the replacement and upgrade of equipment to lower the cost of deployment as well as to improve the efficiency for our cloud-based architecture.

Our business is based on a recurring revenue model. Our customers pay a subscription fee to license the various components of our SaaS platform for a contract term that is typically one to three years. At the end of the license term, customers may renew their subscription and in each year since the launch of our first solution in 2003, we have maintained a renewal rate with our existing customers of 90% or higher. We derive this retention rate by calculating the total annually recurring subscription revenue from customers currently using our SaaS platform and dividing it by the total annually recurring subscription revenue from both these current customers as well as all business lost through non-renewal.

We market and sell our solutions worldwide both directly through our sales teams and indirectly through a hybrid model where our sales organization actively assists our network of distributors and resellers. We also derive a lesser portion of our total revenue from the license of our solutions to strategic partners who offer our solutions in conjunction with one or more of their own products or services.

Our solutions are designed to be implemented, configured and operated without the need for any training or professional services. We offer various training and professional services for those customers that seek to develop deeper expertise in the use of our solutions or would like assistance with complex configurations or the importing of data. In some cases, we provide a hardware appliance to those customers that elect to host elements of our solution behind their firewall. Increasing adoption of virtualization in the data center has led to a decline in the sales of our hardware appliances and a shift towards our software-based virtual appliances, which are delivered as a download via the Internet. Our hardware and services offerings carry lower margins and are provided as a courtesy to our customers. We expect the overall proportion of revenue derived from the hardware and services offerings to generally remain below 5% of our total revenue.

Historically, the majority of our revenue has been derived from our customers in the United States. We believe the markets outside of the United States offer an opportunity for growth and we intend to make additional investments in sales and marketing to expand in these markets. Revenue from customers outside of the United States grew by 2726% for the ~~three~~six months ended ~~March~~June 3130, 2021 as compared to the prior year period, representing 2322% of our total revenue for the period. In terms of customer concentration, two partners accounted for 13% and 11%, respectively, of our total revenue for the three months ended ~~March~~June 3130, 2021. ~~Two partners accounted for 12%~~ and ~~11%, respectively, of our total revenue for~~ the three months ended ~~March~~June 3130, 2020. These partners sold to a number of end-users, none of which accounted for more than 10% of our total revenue. The partners’ sales were spread across many individual customers, all of which have a direct relationship with us as part of their access to our demand services.

We have not been profitable to date and will need to grow revenue at a rate faster than our investments in cost of revenue and operating expenses in order to achieve profitability, as discussed in more detail below.

Significant Developments

In March 2020, the World Health Organization declared the outbreak of the COVID-19 pandemic, which continues to spread throughout the U.S. and the world and has resulted in authorities implementing numerous measures to contain the virus, including travel bans and restrictions, quarantines, shelter-in-place orders, and business limitations and shutdowns. The Company’s overall financial results and operations were modestly impacted by the COVID-19 outbreak in 2020 and the first ~~quarter~~half of 2021. The Company’s travel expense and marketing expense for in-person events were decreased due to global restrictions on travel issued by most major nations where the Company does business. We have shifted our internal annual Sales Kick Off conference, which was held in January 2021, to a virtual-only conference and in the near term we have changed our customer, employee and industry events to virtual-only formats. In addition, see Part II-Item 1A, “Risk Factors,”

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~~changed our customer, employee and industry events to virtual-only formats. In addition, see Part II-Item 1A, “Risk Factors,”~~ included herein for risks associated with pandemics in general and COVID-19 specifically. The extent to which the COVID-19 outbreak impacts our financial results and operations going forward will depend on future developments which are highly uncertain and cannot be predicted, including new information which may emerge concerning the severity of the outbreak and the actions being taken to contain and treat it.

We are taking a variety of measures to ensure the availability and functioning of our critical infrastructure, to promote the safety and security of our employees and to support the communities in which we operate. These measures include requiring remote working arrangements for employees where practicable. We are following public and private sector policies and initiatives to reduce the transmission of COVID-19, such as the imposition of travel restrictions, the promotion of social distancing and the adoption of work-from-home arrangements, and all of these policies and initiatives could impact our operations. The COVID-19 pandemic presents extraordinary challenges in predicting future performance, and while we have modeled many scenarios and associated outcomes, there may be events or trends that are more dire than we have modeled given the unique nature of this event. In particular, we are monitoring COVID-19’s effects on our business across many dimensions, including its broad effects on customers in highly impacted industries and on key ~~Asian~~markets ~~and European economies~~ as they each attempt to recover. These dimensions may change as the pandemic and the response to the pandemic evolve. Some of our customers impacted by COVID-19 ~~seek~~furloughed ~~to manage cash by executing shorter contract durations~~ or bylaid-off ~~furloughing~~employees orto ~~laying~~manage ~~off employees~~cash, especially in highly impacted industries such as travel and hospitality. Other customers are choosing to slow or defer projects, especially those in highly impacted industries and with complex projects requiring large archiving imports that rely heavily on third party resources to manage and execute. We will continue to monitor the impact of the COVID-19 pandemic and continually assess its potential effects on our business and our outlook, the actual results of which will largely depend on future developments, including the duration and spread of the outbreak as well as the varied impacts to our customer base by region or industry, which cannot be accurately predicted and are uncertain.

Key Opportunities and Challenges

The total costs associated with the teams tasked with closing business with new customers and additional business with our existing customers have represented more than 90% of our total sales and marketing costs since 2008. Although we expect customers to be profitable over the duration of the customer relationship, the upfront costs typically exceed related revenue during the earlier periods of a contract. As a result, while our practice of invoicing our customers for the entire amount of the contract at the start of the term provides us with a relatively immediate contribution to cash flow, the revenue is recognized ratably over the term of the contract, and hence contributions toward operating income are limited in the period where the sales and marketing costs are incurred. Accordingly, an increase in the mix of new customers as a percentage of total customers would likely negatively impact our near-term operating results. On the other hand, we expect that an increase in the mix of existing customers as a percentage of total customers would positively impact our operating results over time. As we accumulate customers that continue to renew their contracts, we anticipate that our mix of existing customers will increase, contributing to a decrease in our sales and marketing costs as a percentage of total revenue and a commensurate improvement in our operating income.

As part of maintaining our SaaS platform, we provide ongoing updates and enhancements to the platform services both in terms of the software as well as the underlying hardware and data center infrastructure. These updates and enhancements are provided to our customers at no additional charge as part of the subscription fees paid for the use of our platform. While more traditional products eventually become obsolete and require replacement, we are constantly updating and maintaining our cloud-based services and as such they operate with a continuous product life cycle. Much of this work is designed to both maintain and enhance the customers’ experience over time while also lowering our costs to deliver the service. Our SaaS platform is a shared infrastructure that is used by all of our customers. Accordingly, the costs of the platform are spread in a relatively uniform manner across the entire customer base and no specific infrastructure elements are directly attached to any particular customer. As such, in the event that a customer chooses to not renew its subscription, the underlying resources are reallocated either to new customers or to accommodate the expanding needs of our existing customers and, as a result, we do not believe that the loss of any particular customer has a meaningful impact on our gross profit as long as we continue to grow our customer base.

Historically our customers have primarily used our cybersecurity and compliance solutions with email messaging content. Increasingly, customers are also adopting many of our emerging solutions as part of a people-centric approach to cybersecurity, which focuses on identifying and mitigating risks posed by individual users and the attacks that target them. Our people-centric portfolio includes CASB, Isolation, Insider Threat Management, and Proofpoint Security Awareness Training, many of which provide cyber resiliency across other vectors such as cloud, web and endpoint as well as security awareness training and phishing simulation.

29With the majority of our business, we invoice our customers for the entire contract amount at the start of the term and these amounts are recorded as deferred revenue on our balance sheet, with the dollar weighted average duration of these

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With the majority of our business, we invoice our customers for the entire contract amount at the start of the term and these amounts are recorded as deferred revenue on our balance sheet, with the dollar weighted average duration of these contracts for any given period over the past three years typically ranging from 14 to 20 months. As a result, while our practice of invoicing customers for the entire amount of the contract at the start of the term provides us with a relatively immediate contribution to cash flow, the revenue is recognized ratably over the term of the contract, and hence contributions toward operating income are realized over an extended period. As such, our efforts to improve our profitability require us to invest far less in operating expenses than the cash flow generated by our business might otherwise allow. As we strive to invest in an effort to continue to increase the size and scale of our business, we expect that the level of investment afforded by our growth in revenue should be sufficient to fund the investments needed to drive revenue growth and broaden our product line.

Considering all of these factors, we do not expect to be profitable on a GAAP basis in the near term and in order to achieve profitability we will need to grow revenue at a rate faster than our investments in operating expenses and cost of revenue.

We intend to grow our revenue through acquiring new customers by investing in our sales and marketing activities. We believe that an increase in new customers in the near term will result in a larger base of renewal customers, which, over time, we expect to be more profitable for us.

Sales and marketing is our largest expense and hence a significant contributing factor to our operating losses. We believe that our opportunity to improve our return on investment on sales and marketing costs relies primarily on our ongoing ability to cost-effectively renew our business with existing customers, thereby lowering our overall sales and marketing costs as a percentage of revenue as the mix of revenue derived from this more profitable renewal activity increases over time. Therefore, we anticipate that our initial significant investments in sales and marketing activities will, over time, generate a larger base of more profitable customers. Cost of subscription revenue is also a significant expense for us, and we expect to continue to build on the improvements over the past years, such as in replacing third-party technology with our proprietary technology and improving the utilization of our fixed investments in equipment and infrastructure, in order to provide the opportunity for improved subscription gross margins over time. Although we plan to continue enhancing our solutions, we intend to lower our rate of investment in research and development as a percentage of revenue over time by deriving additional revenue from our existing solutions rather than by adding entirely new categories of solutions. In addition, as personnel costs are one of the primary drivers of the increases in our operating expenses, we plan to reduce our historical rate of headcount growth over time.

Key Metrics

We regularly review a number of metrics, including the following key metrics presented in the table below, to evaluate our business, measure our performance, identify trends in our business, prepare financial projections and make strategic decisions. Many of these key metrics, such as non-GAAP gross margin, billings and free cash flow, are non-GAAP measures. This non-GAAP information is not necessarily comparable to non-GAAP information of other companies. Users of this financial information should consider the types of events and transactions for which adjustments have been made.

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			2021			2020
Total revenue	$	~~287~~308,~~831~~653		$	~~249~~258,~~774~~438		$	596,484		$	508,212
Growth		1519	%		2321	%		17	%		22	%
Gross margin percentage		7475	%		7274	%		75	%		73	%
Non-GAAP gross margin		81	%		7980	%		81	%		80	%
Billings (non-GAAP)	$	~~276~~328,~~741~~597		$	~~237~~250,~~989~~018		$	605,338		$	488,007
Growth		1631	%		118	%		24	%		9	%
Free cash flows (non-GAAP)	$	8854,~~475~~806		$	7918,~~815~~820		$	143,281		$	98,635

Non-GAAP gross margin

We define non-GAAP gross margin as non-GAAP gross profit divided by GAAP revenue. We define non-GAAP gross profit as GAAP gross profit, adjusted to exclude stock-based compensation expense and the amortization of intangibles associated with acquisitions. We consider this non-GAAP financial measure to be a useful metric for management and investors because it excludes the effect of stock-based compensation expense and the amortization of intangibles associated with acquisitions so that our management and investors can compare our business operating results over multiple periods, and compare our financial results with other companies in its industry, many of which present similar non-GAAP financial measure. However, there are a number of limitations related to the use of non-GAAP gross margin versus gross margin calculated in accordance with GAAP. For example, stock-based compensation has been and will continue to be for the

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measure. However, there are a number of limitations related to the use of non-GAAP gross margin versus gross margin calculated in accordance with GAAP. For example, stock-based compensation has been and will continue to be for the foreseeable future a significant recurring expense in our business. Stock-based compensation is an important part of our employees’ compensation and impacts their performance. In addition, the components of the costs that we exclude in our calculation of non-GAAP gross margin may differ from the components that our peer companies exclude when they report their non-GAAP results. Management compensates for these limitations by providing specific information regarding the GAAP amounts excluded from non-GAAP gross margin and evaluating non-GAAP gross margin together with gross margin calculated in accordance with GAAP.

The following table presents the reconciliation of gross margin to Non-GAAP gross margin for the three and six months ended ~~March~~June 3130, 2021 and 2020:

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			2021			2020
GAAP gross profit	$	~~214~~231,~~311~~574		$	~~180~~190,~~843~~863		$	445,885		$	371,706
GAAP gross margin		7475	%		7274	%		75	%		73	%
Plus:
Stock-based compensation expense		7,~~075~~552			6,~~913~~643			14,627			13,556
Amortization expense of intangible assets		10,~~616~~719			9,~~938~~992			21,335			19,930
Non-GAAP gross profit	$	~~232~~249,~~002~~845		$	~~197~~207,~~694~~498		$	481,847		$	405,192
Non-GAAP gross margin		81	%		7980	%		81	%		80	%

Billings

We have included billings, a non‑GAAP financial measure, in this report because it is a key measure used by our management and board of directors to manage our business and monitor our near-term cash flows. We define billings as revenue recognized plus the change in deferred revenue and customer prepayments less the change in unbilled accounts receivable from the beginning to the end of the period, but excluding additions to deferred revenue and customer prepayments from acquisitions. We have provided a reconciliation between total revenue, the most directly comparable GAAP financial measure, and billings. Accordingly, we believe that billings provide useful information to investors and others in understanding and evaluating our operating results in the same manner as our management and board of directors.

Our use of billings as a non-GAAP measure has limitations as an analytical tool, and you should not consider it in isolation or as a substitute for revenue or an analysis of our results as reported under GAAP. Some of these limitations are:

•

Billings are not a substitute for revenue, as trends in billings are not necessarily directly correlated to trends in revenue;

•

Billings are affected by a combination of factors including the timing of renewals, the sales of our solutions to both new and existing customers, the relative duration of contracts sold, and the relative amount of business derived from strategic partners. As each of these elements has unique characteristics in the relationship between billings and revenue, our billings activity is not necessarily closely correlated to revenue; and

•

Other companies, including companies in our industry, may not use billings, may calculate billings differently, or may use other financial measures to evaluate their performance, all of which reduce the usefulness of billings as a comparative measure.

Our deferred revenue consists of amounts that have been invoiced but have not been recognized as revenue as of the period end. Customer prepayments represent billed amounts for which the contract can be terminated and the customer has a right of refund. Unbilled accounts receivable represent amounts for which we have recognized revenue, pursuant to our revenue recognition policy, for subscription software already delivered and professional services already performed, but billed in arrears and for which we believe we have an unconditional right to payment.

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The following table presents the reconciliation of total revenue to billings for the three and six months ended ~~March~~June 3130, 2021 and 2020:

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
(In thousands)	2021			2020			2021			2020
Total revenue	$	~~287~~308,~~831~~653		$	~~249~~258,~~774~~438		$	596,484		$	508,212
Deferred revenue and customer prepayments
Ending		~~900~~919,~~925~~599			~~787~~776,~~098~~255			919,599			776,255
Beginning		~~904~~900,~~126~~925			~~797~~787,~~173~~098			904,126			797,173
Net change		(318,~~201~~674	)		(10,~~075~~843	)		15,473			(20,918	)
Unbilled accounts receivable
Ending		21,~~673~~403			31,~~965~~542			1,403			1,542
Beginning		12,~~877~~673			23,~~255~~965			1,877			2,255
Net change		~~(796~~1,270	)		(12,~~710~~423	)		474			713
Less: deferred revenue and customer prepayments contributed by acquisitions		~~(7,093~~—	)		—			(7,093	)		—
Billings	$	~~276~~328,~~741~~597		$	~~237~~250,~~989~~018		$	605,338		$	488,007

Free cash flows

We define free cash flow as net cash provided by operating activities minus capital expenditures. We consider free cash flow to be a liquidity measure that provides useful information to management and investors about the amount of cash generated by the business that, after the acquisition of property and equipment, can be used for strategic opportunities, including investing in our business, making strategic acquisitions, and strengthening the balance sheet. Analysis of free cash flow facilitates management’s comparisons of our operating results to competitors’ operating results. A limitation of using free cash flow versus the GAAP measure of net cash provided by operating activities as a means for evaluating our company is that free cash flow does not represent the total increase or decrease in the cash balance from operations for the period because it excludes cash used for capital expenditures during the period. Management compensates for this limitation by providing information about our capital expenditures on the face of the cash flow statement and in the “Liquidity and Capital Resources” section below.

	Three Months Ended March 31,
	Three Months Ended June 30,						Six Months Ended June 30,
(In thousands)	2021			2020			2021			2020
GAAP cash flows provided by operating activities:	$	9560,~~090~~860		$	9230,~~174~~610		$	155,950		$	122,784
Less:
Purchase of property and equipment		(6,~~615~~054	)		(1211,~~359~~790	)		(12,669	)		(24,149	)
Non-GAAP free cash flows	$	8854,~~475~~806		$	7918,~~815~~820		$	143,281		$	98,635

Critical Accounting Policies and Estimates

The discussion and analysis of our financial condition and results of operations is based upon our accompanying Condensed Consolidated Financial Statements, which have been prepared in accordance with U.S. GAAP. The preparation of these financial statements requires us to make estimates, assumptions and judgments that can have significant impact on the reported amounts of assets and liabilities, revenues and expenses, and related disclosure of contingent assets and liabilities at the date of our financial statements. We base our estimates, assumptions and judgments on historical experience and various other factors that we believe to be reasonable under the circumstances. Actual results may differ from these estimates under different assumptions or conditions. On a regular basis, we evaluate our estimates, assumptions and judgments and make changes accordingly.

We believe that the estimates, assumptions and judgments involved in revenue recognition, deferred commissions, stock-based compensation expense, fair value of assets acquired and liabilities assumed in business combinations, impairment assessment of goodwill, intangible assets and other long-lived assets, loss contingency, and recognition and measurement of current and deferred income taxes have the greatest potential impact on our accompanying Condensed Consolidated Financial Statements, and consider these to be our critical accounting estimates. Historically, our estimates, assumptions and judgments relative to our critical accounting policies have not differed materially from actual results. The critical accounting estimates associated with these policies are described in our 2020 Annual Report on Form 10-K, under “Management’s Discussion and Analysis of Financial Condition and Results of Operations.”

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Components of Our Results of Operations

Revenue

We derive our revenue primarily through the license of various solutions and services on our security-as-a-service platform on a subscription basis, supplemented by the sales of training, professional services and hardware depending upon our customers’ requirements.

Subscription. We license our platform and its associated solutions and services on a subscription basis. The fees are charged on a per user, per year basis. Subscriptions are typically one to three years in duration. We invoice our customers upon signing for the entire term of the contract. The invoiced non-cancellable amounts billed in advance are treated as deferred revenue on the balance sheet and are recognized ratably, in accordance with the appropriate revenue recognition guidelines, over the term of the contract. We also derive a portion of our subscription revenue from the license of our solutions to strategic partners. We bill these strategic partners monthly. We expect our subscription revenue will continue to grow and remain above 95% of our total revenue.

Hardware and services. We provide hardware appliances as a convenience to our customers and as such it represents a small part of our business. Our solutions are designed to be implemented, configured and operated without the need for any training or professional services. For those customers that seek to develop deeper expertise in the use of our solutions or would like assistance with complex configurations or the importing of data, we offer various training and professional services. We typically invoice the customer for hardware at the time of shipment. We typically invoice customers for services at the time the order is placed and recognize this revenue as the services are performed. On occasion, customers may retain us for special projects such as archiving import and export services; these types of services are recognized upon completion of the project. We expect the overall proportion of revenue derived from hardware and service offerings to generally remain below 5% of our total revenue.

Cost of Revenue

Our cost of revenues consists of cost of subscription revenue and cost of hardware and services revenue. Personnel costs, which consist of salaries, benefits, bonuses, stock-based compensation, data center costs and hardware costs, are the most significant components of our cost of revenues. We expect personnel costs to continue to increase in absolute dollars as we hire new employees to continue to grow our business.

Cost of Subscription Revenue. Cost of subscription revenue primarily includes personnel costs, consisting of salaries, benefits, bonuses, and stock-based compensation, for employees who provide support services to our customers and operate our data centers. Other costs include fees paid to contractors who supplement our support and data center personnel; expenses related to the use of third-party data centers in both the United States and internationally; depreciation of data center equipment; amortization of licensing fees and royalties paid for the use of third-party technology; amortization of internally developed intangible assets; and the amortization of intangible assets acquired through business combinations. Growth in subscription revenue generally consumes production resources, requiring us to gradually increase our cost of subscription revenue in absolute dollars as we expand our investment in data center equipment, the third-party data center space required to house this equipment, and the personnel needed to manage this higher level of activity.

Cost of Hardware and Services Revenue. Cost of hardware and services revenue includes personnel costs for employees who provide training and professional services to our customers as well as the cost of server hardware shipped to our customers that we procure from third parties and configure with our software solutions.

Operating Expenses

Our operating expenses consist of research and development, sales and marketing, and general and administrative expenses. Personnel costs, which consist of salaries, benefits, bonuses, and stock-based compensation, are the most significant component of our operating expenses. Our headcount has increased from 2,613 employees as of December 31, 2018 to 3,658 employees as of December 31, 2020. As a result of this growth in headcount, operating expenses have increased significantly over these periods. We expect personnel costs to continue to increase in absolute dollars as we hire new employees to continue to grow our business.

Research and Development. Research and development expenses include personnel costs, consulting services and depreciation. We believe that these investments have played an important role in broadening the capabilities of our platform over the course of our operating history, enhancing the relevance of our solutions in the market in general and helping us to retain our customers over time. We expect to continue to devote substantial resources to research and development in an effort to continuously improve our existing solutions as well as to develop new offerings. We believe that these investments

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are necessary to maintain and improve our competitive position. However, over the longer term, we intend to monitor these costs so as to decrease this spending as a percentage of total revenue. Our research efforts include both software developed for our internal use on behalf of our customers as well as software elements to be used by our customers in their own facilities. To date, our capitalized costs on software developed for internal use on behalf of our customers were not material. For the software developed for use on our customers’ premises, the costs associated with the development work between technological feasibility and the general availability has not been material and as such we have not capitalized any of these development costs to date.

Sales and Marketing. Sales and marketing expenses include personnel costs, sales commissions, and other costs including travel and entertainment, marketing and promotional events, public relations and marketing activities. These costs also include amortization of intangible assets as a result of our past acquisitions. Due to our continued investment in growing our sales and marketing operations, both domestically and internationally, headcount increases were reflected in higher compensation expense consistent with our revenue growth. Our sales personnel are typically not immediately productive, and therefore the increase in sales and marketing expenses we incur when we add new sales representatives is not immediately offset by increased revenue and may not result in increased revenue over the long-term if these new sales people fail to become productive. The timing of our hiring of new sales personnel and the rate at which they generate incremental revenue will affect our future financial performance. We expect that sales and marketing expenses will continue to increase in absolute dollars and be among the most significant components of our operating expenses.

General and Administrative. General and administrative expenses consist of personnel costs, consulting services, audit fees, tax services, legal expenses and other general corporate items. As a result of our operational growth, we expect our general and administrative expenses to increase in absolute dollars in future periods as we continue to expand our operations and hire additional personnel.

Interest Expense

Interest expense consists of interest expense related to our convertible senior notes.

Other Income, Net

Other income, net, consists primarily of interest income earned on our cash, cash equivalents and short-term investments, and the net effect of foreign currency transaction gains and losses.

Income Taxes

For most of the prior years, our income tax expense or benefit were primarily related to state and foreign income taxes. As we have incurred operating losses in all periods to date and recorded a full valuation allowance against our deferred tax assets, we had not historically recorded a provision for federal income taxes. Realization of any of our deferred tax assets depends upon future earnings, the timing and amount of which are uncertain. Utilization of our net operating losses and research and development credits may be subject to substantial annual limitation due to the ownership change limitations provided by the Internal Revenue Code and similar state provisions. Analyses have been conducted to determine whether an ownership change had occurred since inception. The analyses have indicated that although ownership changes have occurred in prior years, the net operating losses and research and development credits would not expire before utilization as a result of the ownership change. In the event we have subsequent changes in ownership, net operating losses and research and development credit carryovers could be limited and may expire unutilized as a result of the subsequent ownership change.

Recent Accounting Pronouncements

Refer to Note 1 “The Company and Summary of Significant Accounting Policies” to our condensed consolidated financial statements in Part I, Item 1 of this Quarterly Report on Form 10-Q for a full description of recent accounting pronouncements.

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Results of Operations

The following table is a summary of our consolidated statements of operations and results of operations as a percentage of our total revenue for those periods.

	Three Months Ended March 31,
	Three Months Ended June 30,												Six Months Ended June 30,
	2021						2020						2021						2020
( In thousands, except for percentages)	Amount			% of revenue			Amount			% of revenue			Amount			% of revenue			Amount			% of revenue
Revenue:
Subscription	$	~~283~~303,~~612~~510			9998	%	$	~~244~~254,~~069~~892			9899	%	$	587,122			98	%	$	498,961			98	%
Hardware and services		45,~~219~~143			12			53,~~705~~546			21			9,362			2			9,251			2
Total revenue		~~287~~308,~~831~~653			100			~~249~~258,~~774~~438			100			596,484			100			508,212			100
Cost of revenue:
Subscription		6467,~~007~~659			22			59,~~848~~193			2423			131,666			22			119,041			23
Hardware and services		9,~~513~~420			43			98,~~083~~382			43			18,933			3			17,465			4
Total cost of revenue		7377,~~520~~079			2625			6867,~~931~~575			2826			150,599			25			136,506			27
Gross profit		~~214~~231,~~311~~574			7475			~~180~~190,~~843~~863			7274			445,885			75			371,706			73
Operating expense:
Research and development		8081,~~518~~319			2826			6970,~~895~~602			2827			161,837			27			140,497			27
Sales and marketing		~~143~~142,~~144~~949			5046			~~123~~116,~~162~~279			4945			286,093			48			239,441			47
General and administrative		3254,~~711~~664			1118			2914,~~555~~812			126			87,375			15			44,367			9
Total operating expense		~~256~~278,~~373~~932			8990			~~222~~201,~~612~~693			8978			535,305			90			424,305			83
Operating loss		(4247,~~062~~358	)		(15	)		(4110,~~769~~830	)		(174	)		(89,420	)		(15	)		(52,599	)		(10	)
Interest expense		(1,~~528~~533	)		—			(1,~~524~~525	)		(1	)		(3,061	)		—			(3,049	)		(1	)
Other income, net		365			—			4,621			2
Other (expense) income, net		(1,712	)		(1	)		(1,092	)		—			(1,347	)		—			3,529			1
Loss before income taxes		(4350,~~225~~603	)		(1516	)		(3813,~~672~~447	)		(165	)		(93,828	)		(15	)		(52,119	)		(10	)
Provision for income taxes		(2,~~094~~312	)		(1	)		(281,~~169~~660	)		(111	)		(4,406	)		(1	)		(29,829	)		(6	)
Net loss	$	(4552,~~319~~915	)		(1617	)%	$	(6615,~~841~~107	)		(276	)%	$	(98,234	)		(16	)%	$	(81,948	)		(16	)%

Comparison of the three and six months ended ~~March~~June 3130, 2021 and 2020:

Revenue

	Three Months Ended March 31,
	Three Months Ended June 30,							Six Months Ended June 30,
( In thousands, except for percentages)	2021		2020		% Change			2021		2020		% Change
Revenue
Subscription	$	~~283~~303,~~612~~510	$	~~244~~254,~~069~~892		1619	%	$	587,122	$	498,961		18	%
Hardware and services		45,~~219~~143		53,~~705~~546		~~(26~~45	)%		9,362		9,251		1	%
Total revenue	$	~~287~~308,~~831~~653	$	~~249~~258,~~774~~438		1519	%	$	596,484	$	508,212		17	%

Subscription revenue for the three and six months ended ~~March~~June 3130, 2021 increased $3948.56 million, or 1619%, and $88.2 million, or 18%, respectively, as compared to the corresponding ~~period~~periods last year. The increase was primarily due to a $2536.3 million and $61.6 million, respectively, increase in subscription revenue contributed from the United States. To a lesser extent, for the same ~~period~~periods, there ~~was~~were anincreases ~~increase~~ of $1412.23 million, and $26.5 million, respectively, in revenue contributed from international locations. The increase in subscription revenue was due to the increased demand for our solutions, increase in add-on activity and renewal rate being 90% or higher. Additionally, the revenue recognized from acquired deferred revenue related to our acquisitions was $12.85 million and $4.1 million, respectively, in the three and six months ended ~~March~~June 3130, 2021, as compared to $2.1.5 million and $3.6 million, respectively, in the three months and six ended ~~March~~June 3130, 2020.

Hardware and services revenue for the three and six months ended ~~March~~June 3130, 2021 ~~decreased~~increased $1.56 million, or 2645%, and $0.1 million, or 1%, respectively, as compared to the corresponding ~~period~~periods last year. The ~~decrease~~increase was primarily due to aincreases ~~decrease~~in professional services of $1.8 million and $1.7 million, respectively, offset by decreases in hardware revenue of $0.2 million and $1.46 million, respectively, for the three and six months ended June 30, 2021.

~~Cost of Revenue~~36

	Three Months Ended March 31,
( In thousands, except for percentages)	2021		2020		% Change
Cost of revenue
Subscription	$	64,007	$	59,848		7	%
Hardware and services		9,513		9,083		5	%
Total cost of revenue	$	73,520	$	68,931		7	%

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Cost of subscription revenue for the three months ended March 31, 2021 increased $4.2 million, or 7%, compared to the corresponding period last year. The increases were primarily due to $3.9 million increases in operations-related expenses including higher network expense from increased data usage, depreciation expense as a result of higher capital expenditures to support our growth, intangible amortization expense of developed technology from the acquisitions, and higher compensation costs due to increase in headcount. Support-related expenses increased $1.0 million primarily due to higher headcount related costs. Revenue

Cost of hardware and services revenue for the three months ended March 31, 2021 increased $0.4 million, or 5%, as compared to the corresponding period last year, primarily due to increases in professional service costs of $1.1 million as our headcount increased. The cost of hardware units sold decreased $0.8 million for the three months ended March 31, 2021.

	Three Months Ended June 30,							Six Months Ended June 30,
( In thousands, except for percentages)	2021		2020		% Change			2021		2020		% Change

Cost of revenue
Subscription	$	67,659	$	59,193		14	%	$	131,666	$	119,041		11	%
Hardware and services		9,420		8,382		12	%		18,933		17,465		8	%
Total cost of revenue	$	77,079	$	67,575		14	%	$	150,599	$	136,506		10	%

Cost of subscription revenue for the three and six months ended June 30, 2021 increased $8.5 million, or 14%, and $12.6 million, or 11%, respectively, compared to the corresponding periods last year. The increases were primarily due to $5.2 million and $9.2 million, respectively, increases in operations-related expenses including higher network expense from increased data usage, depreciation expense as a result of higher capital expenditures to support our growth, intangible amortization expense of developed technology from the acquisitions, and higher compensation costs due to increase in headcount. Support-related expenses increased $3.7 million and $4.8 million, respectively, primarily due to higher headcount related costs.

Cost of hardware and services revenue for the three and six months ended June 30, 2021 increased $1.0 million, or 12%, and $1.5 million, or 8%, respectively, as compared to the corresponding periods last year, primarily due to increases in professional service costs of $1.1 million and $2.2 million, respectively, as our headcount increased. The cost of hardware units sold decreased $0.2 million and $1.0 million, respectively, for the three and six months ended June 30, 2021.

Operating Expenses

	Three Months Ended March 31,
	Three Months Ended June 30,									Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			% Change			2021			2020			% Change
Research and development	$	8081,~~518~~319		$	6970,~~895~~602			15	%	$	161,837		$	140,497			15	%
Percent of total revenue		2826	%		2827	%					27	%		27	%

Research and development expenses increased $10.67 million, or 15%, and $21.3 million, or 15%, respectively, for the three and six months ended ~~March~~June 3130, 2021, as compared to the corresponding ~~period~~periods last year. The increase in headcount on a worldwide basis resulted in increased personnel-related expenses of $9.85 million and $19.3 million, respectively, and a corporate expense increase of $2.1 million and $3.78 million, respectively. The increase was partially offset by a decrease of $0.57 million and $1.2 million, respectively, in outside service-related expense, primarily due to a decrease in consulting costs~~, and a travel related expense decrease of $0~~.~~2 million.~~

	Three Months Ended March 31,
	Three Months Ended June 30,									Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			% Change			2021			2020			% Change
Sales and marketing	$	~~143~~142,~~144~~949		$	~~123~~116,~~162~~279			1623	%	$	286,093		$	239,441			19	%
Percent of total revenue		5046	%		4945	%					48	%		47	%

Sales and marketing expenses increased $2026.07 million, or 1623%, and $46.7 million, or 19%, respectively, for the three and six months ended ~~March~~June 3130, 2021, as compared to the corresponding ~~period~~periods last year. The increase in headcount on a worldwide basis resulted in increased personnel-related and commissions expenses of $2421.5 million and $45.9 million, respectively, which ~~include~~included increases in stock-based compensation expense of $86.7 million and $15.4 million, respectively. Corporate and facilities expenses increased $32.36 million and $5.9 million, respectively, primarily due to higher headcount. ~~The~~Marketing ~~increases~~events ~~were~~and ~~partially~~consulting ~~offset~~expense byincreased ~~the~~$2.8 ~~decreases~~million inand ~~travel expense of~~ $62.49 million, respectively. Additionally, for the ~~three~~six months ended ~~March~~June 3130, 2021, as compared to the same period last year, ~~primarily~~the ~~due~~increases towere ~~travel~~partially ~~restrictions~~offset ~~imposed~~ by ~~COVID-19.~~the ~~Additionally,~~decreases in intangible amortization expense ~~decreased~~of $0.9 million ~~for~~and ~~the~~travel ~~three~~expense ~~months~~of ~~ended~~$6.3 ~~March 31, 2021 as compared to the same period last year~~million.

	Three Months Ended March 31,
	Three Months Ended June 30,									Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			% Change			2021			2020			% Change
General and administrative	$	3254,~~711~~664		$	2914,~~555~~812			11269	%	$	87,375		$	44,367			97	%
Percent of total revenue		1118	%		126	%					15	%		9	%

General and administrative expenses increased $339.29 million, or 11269%, and $43.0 million, or 97%, respectively, for the three and six months ended ~~March~~June 3130, 2021 as compared to the corresponding ~~period~~periods last year. ~~Acquisition~~Personnel-related ~~costs~~expense increased $116.29 million ~~due~~and to$16.7 ~~the~~million ~~timing~~for ofthe ~~acquisitions,~~three and ~~litigation~~six ~~related~~months ~~expense~~ended ~~increased~~June ~~$2.7~~30, ~~million~~2021, respectively, primarily due to ~~trade~~higher ~~secret~~headcount ~~litigation~~and ~~brought~~reversal byof uscertain ~~against~~PSU aexpenses ~~third~~in ~~party.~~the ~~Outside~~second ~~service~~quarter ~~expense decreased~~ of $02020.5 ~~million~~Acquisition ~~for~~costs ~~the~~increased ~~three months ended March 31, 2021, as compared to the same period last year~~$18.9

~~Interest Expense~~37

	Three Months Ended March 31,
( In thousands, except for percentages)	2021			2020			% Change
Interest expense	$	(1,528	)	$	(1,524	)		0	%

Interest expense change was not material for the three months ended March 31, 2021, as compared to the corresponding period last year.

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~~Other~~million ~~Income~~and $20.0 million, ~~Net~~respectively, primarily due to the announced transaction to be acquired by Thoma Bravo in the third quarter. Litigation related expense increased $3.1 million and $5.8 million, respectively, primarily due to trade secret litigation brought by us against a third party.

	Three Months Ended March 31,
( In thousands, except for percentages)	2021		2020		% Change
Other income, net	$	365	$	4,621		(92	%)

Interest Expense

Other income, net decreased $4.3 million for the three months ended March 31, 2021, as compared to the corresponding period last year, primarily due to a $2.9 million decrease in interest income from cash and investments, and a $1.4 million decrease in foreign currency translation gain.

	Three Months Ended June 30,									Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			% Change			2021			2020			% Change

Interest expense	$	(1,533	)	$	(1,525	)		1	%	$	(3,061	)	$	(3,049	)		0	%

Interest expense change was not material for the three and six months ended June 30, 2021, as compared to the corresponding periods last year.

Other (Expense) Income, Net

	Three Months Ended June 30,									Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			% Change			2021			2020		% Change

Other (expense) income, net	$	(1,712	)	$	(1,092	)		57	%	$	(1,347	)	$	3,529		(138	)%

Other expense, net increased $0.6 million for the three months ended June 30, 2021, as compared to the corresponding period last year, primarily due to a $0.3 million decrease in interest income from cash and investments, and a $0.2 million increase in foreign currency translation loss.

Other expense, net increased $4.9 million for the six months ended June 30, 2021, as compared to the corresponding period last year, primarily due to a $3.2 million decrease in interest income from cash and investments, and a $1.6 million increase in foreign currency translation loss.

Provision for Income Taxes

	Three Months Ended March 31,
	Three Months Ended June 30,									Six Months Ended June 30,
( In thousands, except for percentages)	2021			2020			% Change			2021			2020			% Change
Provision for income taxes	$	(2,~~094~~312	)	$	(281,~~169~~660	)		~~(93~~39	%)	$	(4,406	)	$	(29,829	)		(85	%)

The provision for income taxes increased $0.7 million, and decreased $2625.14 million, respectively, for the three and six months ended ~~March~~June 3130, 2021, as compared to the corresponding ~~period~~periods last year. The ~~decrease~~increase for the three months ended ~~March~~June 3130, 2021 was primarily due to a $~~27.~~0.5 million ~~expense~~increase of foreign taxes related to aoperations in our non-US subsidiaries, as compared to the corresponding prior period. The decrease for the six months ended June 30, 2021 was primarily due to the transfer of intellectual property between consolidated entities that ~~occurred~~resulted ~~during~~in an additional tax expense of $27.1 million in the ~~three~~six months ended ~~March~~June 3130, 2020, partially offset by a $0.59 million increase in foreign taxes related to operations of our non-U.S. subsidiaries for the six months ended June 30, 2021.

Liquidity and Capital Resources

As of ~~March~~June 3130, 2021, we had $~~882~~929.63 million in cash and cash equivalents. Also refer to Note 8 “Convertible Senior Notes” to the consolidated financial statements for discussion of the 2024 Notes. The Company’s financial condition and liquidity remain strong. Net cash provided by operations was $95156.10 million for the ~~three~~six months ended ~~March~~June 3130, 2021, compared to $92122.28 million for the corresponding period of the prior year. Although there is uncertainty related to the anticipated impact of the COVID-19 outbreak on the Company’s future results, we believe our efficient business model leaves us positioned to manage our business through this crisis as it continues to unfold. We continue to manage all aspects of our business including, but not limited to, monitoring the financial health of our customers, suppliers and other third-party relationships, implementing gross margin enhancement strategies and developing new opportunities for growth. We have also not observed any impairments of our assets or a significant change in the fair value of assets due to the COVID-19 pandemic.

On August 27, 2020, the board of directors approved a share repurchase program under which the Company is authorized to repurchase up to $300.0 million of the Company’s common stock. Repurchases under the Repurchase Program may be made through open market purchases (including through trading plans administered under pre-determined purchasing criteria), block trades and/or privately negotiated transactions, subject to market conditions, applicable legal requirements, and other relevant factors. The timing, volume and nature of the repurchases are at the discretion of management, based on its evaluation of the capital needs of the Company, market conditions, applicable legal requirements and other factors. The Repurchase Program does not have an expiration date and may be suspended or discontinued by the Company at any time without prior notice.

As of March 31, 2021, we had approximately $27.7 million of cash and cash equivalents at our foreign subsidiaries. We estimate that no material U.S. income taxes would have to be provided if all of the undistributed earnings of our foreign subsidiaries were repatriated back to the United States as substantially all earnings from our foreign subsidiaries are previously taxed income.38

On April 25, 2021, we entered into the Merger Agreement pursuant to which affiliates of funds advised by Thoma Bravo have agreed to acquire us for $176.00 per share in an all-cash transaction. We have agreed to various covenants and agreements, including, among others, agreements to conduct our business in the ordinary course during the period between the execution of the Merger Agreement and the effective time of the Merger. In addition, without the consent of Project Kafka Parent, LLC, a Delaware limited liability company (“Parent”), we may not take, authorize, agree or commit to do certain actions outside of the ordinary course of business, including incurring capital expenditures above specified thresholds, issuing additional debt facilities, and repurchasing shares of our outstanding common stock outside of certain limited exceptions. If the Merger Agreement is terminated in certain circumstances, including by us in order to enter into a superior proposal or by Parent because the Board withdraws its recommendation in favor of the Merger, we would be required to pay Parent a termination fee of $368.9 million; provided that a lower fee of $123.0 million will apply with respect to a

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~~termination~~evaluation toof ~~enter~~the ~~into~~capital aneeds ~~superior~~of ~~proposal during~~ the ~~“go-shop”~~Company, ~~period.~~market Weconditions, doapplicable ~~not~~legal ~~believe~~requirements ~~these~~and ~~restrictions~~other ~~will~~factors. ~~prevent~~The usRepurchase ~~from~~Program ~~meeting~~was ~~our~~suspended ~~debt~~in ~~obligations,~~April ~~ongoing~~2021 ~~costs~~when ofthe ~~operations,~~Company ~~working~~entered ~~capital~~into ~~needs~~the orMerger ~~capital expenditure requirements~~Agreement.

As of June 30, 2021, we had approximately $27.7 million of cash and cash equivalents at our foreign subsidiaries. We estimate that no material U.S. income taxes would have to be provided if all of the undistributed earnings of our foreign subsidiaries were repatriated back to the United States as substantially all earnings from our foreign subsidiaries are previously taxed income.

On April 25, 2021, we entered into the Merger Agreement pursuant to which affiliates of funds advised by Thoma Bravo have agreed to acquire us for $176.00 per share in an all-cash transaction. We have agreed to various covenants and agreements, including, among others, agreements to conduct our business in the ordinary course during the period between the execution of the Merger Agreement and the Effective Time of the Merger. In addition, without the consent of Parent, we may not take, authorize, agree or commit to do certain actions outside of the ordinary course of business, including incurring capital expenditures above specified thresholds, issuing additional debt facilities, and repurchasing shares of our outstanding common stock outside of certain limited exceptions. If the Merger Agreement is terminated in certain circumstances, including by us in order to enter into a superior proposal or by Parent because the Board withdraws its recommendation in favor of the Merger, we would be required to pay Parent a termination fee of $368.9 million. We do not believe these restrictions will prevent us from meeting our debt obligations, ongoing costs of operations, working capital needs or capital expenditure requirements.

We plan to grow our customer base by continuing to emphasize investments in sales and marketing to add new customers, expand our customers’ use of our platform, and maintain high renewal rates. We also expect to incur additional cost of subscription revenue in accordance with the resulting growth in our customer base. We believe that the combination of our ongoing improvements in gross margins, the benefits of lower sales and marketing costs associated with our renewal activity, and the fact that our contracts are structured to bill our customers in advance should enable us to improve our cash flow from operations as we grow. Based on our current level of operations and anticipated growth, both of which are expected to be consistent with recent quarters, we believe that our existing sources of liquidity will be sufficient to fund our operations for at least the next 12 months. Our future capital requirements will depend on many factors, including our rate of revenue growth, the expansion of our sales and marketing activities, and the timing and extent of spending to support product development efforts and expansion into new territories, and the timing of introductions of new features and enhancements to our solutions. To the extent that existing cash and cash equivalents and cash from operations are insufficient to fund our future activities, we may need to raise additional funds through public or private equity or debt financing. We have invested, and plan to continue investing in acquiring complementary businesses, applications and technologies, and may continue to make such investments in the future, any of which could also require us to seek equity or debt financing in addition to our 2024 Notes. Additional funds may not be available on terms favorable to us or at all.

Cash Flows

The following table sets forth a summary of our consolidated cash flows for the periods indicated:

	Three Months Ended March 31,
	Six Months Ended June 30,
(In thousands)	2021			2020
Net cash provided by operating activities	$	95155,~~090~~950		$	92122,~~174~~784
Net cash (used in) provided by investing activities	$	(6268,~~053~~107	)	$	64,~~997~~596
Net cash used in financing activities	$	(5667,~~145~~108	)	$	(2416,~~634~~602	)

Operating Activities

Our net loss and cash flows from operating activities are significantly influenced by our investments in headcount and data center operations to support anticipated growth. Our cash flows are also influenced by cash payments from customers. We invoice customers for the entire contract amount at the start of the term, and as such our cash flow from operations is also affected by the length of a customer contract.

Net cash provided by operating activities in the ~~three~~six months ended ~~March~~June 3130, 2021 was $95156.10 million, as compared to $92122.28 million provided in the ~~three~~six months ended ~~March~~June 3130, 2020. The increase of $233.92 million was primarily due to:

• AAn ~~decrease~~increase in ~~net~~stock-based ~~loss~~compensation expense of $2134.54 million due to the increase in headcount and new grants made, and the catch-up adjustments made to performance stock unit expenses in the second quarter of 2020;

~~• An increase in stock-based compensation expense of $9.5 million due to the increase in headcount and new grants made;~~39

• A $12.7 million increase in prepaid expenses and accounts payable change due to the timing of payments;

• A $3.4 million increase in amortization of deferred commissions primarily due to corresponding increase in revenue;

• An increase in deferred revenue change of $2.8 million primarily due to the timing of billings and revenue recognized; and

• A $4.1 million increase in non-cash lease costs and operating lease liabilities due to higher lease costs and the timing of payments.

The increase was partially offset by:

• A decrease in accounts receivable change of $17.4 million due to the timing of customer payments;

• A $29.1 million decrease in accrued liabilities change due to a $15.8 million increase in uncertain tax benefit change as well as the timing of other payments made; and

• A decrease in deferred commission change of $5.7 million primarily due to an increase in billings.

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•

A $43.0 million increase in prepaid expenses and accounts payable change due to the timing of payments;

•

A $7.3 million increase in amortization of deferred commissions primarily due to corresponding increase in revenue;

•

An increase in deferred revenue change of $34.0 million primarily due to the timing of billings and revenue recognized; and

•

A $7.5 million increase in non-cash lease costs and operating lease liabilities due to higher lease costs and the timing of payments.

The increase was partially offset by:

•

An increase in net loss of $16.3 million;

•

A decrease in accounts receivable change of $39.7 million due to the timing of customer payments;

•

A $23.4 million decrease in accrued liabilities change due to a $15.7 million decrease in uncertain tax benefit change as well as the timing of other payments made; and

•

A decrease in deferred commission change of $16.3 million primarily due to an increase in billings.

Investing Activities

Our primary investing activities have consisted of the acquisitions of businesses, the purchase and sale of short-term investments and capital expenditures in support of expanding our infrastructure and workforce. As our business grows, we expect our capital expenditures and our investment activity to continue to increase.

Net cash used in investing activities was $6268.1 million in the ~~three~~six months ended ~~March~~June 3130, 2021 as compared to $74.06 million provided by investing activities in the ~~three~~six months ended ~~March~~June 3130, 2020. The increase in cash used in investing activities of $6972.17 million was primarily due to a $5552.47 million increase in payments for acquired business, and a $3951.2 million decrease in proceeds from maturities of short-term investments, partially offset by a $19.9 million decrease in cash spent to acquire short-term investments, and a $511.75 million decrease in capital expenditures.

Financing Activities

Net cash used in financing activities was $5667.1 million in the ~~three~~six months ended ~~March~~June 3130, 2021 as compared to $2416.6 million used in the ~~three~~six months ended ~~March~~June 3130, 2020. The increase in cash used in financing activities of $3150.5 million was primarily due to $2744.10 million increase in repurchases of commons stock, and a $27.21 million ~~decrease~~increase in ~~proceeds~~withholding ~~from~~taxes ~~common~~paid ~~stock issuance~~ related to ~~employee~~restricted stock ~~plans;~~net ~~and~~share settlement, partially offset by a $20.25 million increase in ~~withholding~~proceeds ~~taxes~~from ~~paid~~common stock issuance related to ~~restricted~~employee stock ~~net share settlement~~plans;.

Off-Balance Sheet Arrangements

During the periods presented, we did not have, nor do we currently have, any relationships with unconsolidated entities or financial partnerships, such as entities often referred to as structured finance or special purpose entities, which would have been established for the purpose of facilitating off-balance sheet arrangements or other contractually narrow or limited purposes. We are therefore not exposed to any financing, liquidity, market or credit risk that could arise if we had engaged in those types of relationships.

Contractual Obligations and Commitments

There were no material changes outside the ordinary course of business during the ~~three~~six months ended ~~March~~June 3130, 2021 to the contractual obligations and commitments disclosed in Management’s Discussion and Analysis of Financial Condition and Results of Operations, set forth in Part II, Item 7, of the Form 10-K.

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ITEM 3. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK.

We have operations both within the United States and internationally, and we are exposed to market risks in the ordinary course of our business. These risks primarily include interest rate, foreign exchange and inflation risks, as well as risks relating to changes in the general economic conditions in the countries where we conduct business. To reduce certain of these risks, we monitor the financial condition of our large clients and limit credit exposure by collecting in advance and setting credit limits as we deem appropriate. In addition, our investment strategy has been to invest in financial instruments that are highly liquid and readily convertible into cash. To date, we have not used derivative instruments to mitigate the impact of our market risk exposures. We have also not used, nor do we intend to use, derivatives for trading or speculative purposes.

Interest Rate Risk

We are exposed to market risk related to changes in interest rates. Our investments primarily consist of money market funds, corporate debt securities, commercial papers, U.S. agency and Treasury securities, and certificates of deposit. As of ~~March~~June 3130, 2021, we had cash and cash equivalents of $~~882~~929.63 million. We didn’t have short-term investments as of ~~March~~June 3130, 2021 and December 31, 2020. The carrying amount of our cash equivalents reasonably approximates fair value, due to the short maturities of these investments. The primary objectives of our investment activities are the preservation of capital, the fulfillment of liquidity needs and the fiduciary control of cash and investments. We do not enter into investments for trading or speculative purposes. Our investments are exposed to market risk due to a fluctuation in interest rates, which may affect our interest income and the fair market value of our investments. Due to the short-term nature of our investment portfolio, we believe only dramatic fluctuations in interest rates would have a material effect on our investments. We do not believe that an immediate 10% increase in interest rates would have a material effect on the fair market value of our portfolio. As such we do not expect our operating results or cash flows to be materially affected by a sudden change in market interest rates.

As of ~~March~~June 3130, 2021, we had an outstanding balance of $920.0 million aggregate principal amount of the 2024 Notes (see Note 8 “Convertible Senior Notes” to our condensed consolidated financial statements in this Quarterly Report on Form 10-Q for information regarding our Convertible Senior Notes). We carry the notes at face value, less unamortized discounts, on our accompanying condensed consolidated balance sheets. Since these notes bear interest at fixed rates, we have no financial statement risk associated with changes in interest rates. However, the fair value of these notes fluctuates as interest rate changes when the market price of our common stock fluctuates.

Foreign Currency Risk

The functional currency for our wholly owned foreign subsidiaries is the U.S. dollar. Accordingly, the subsidiaries remeasure monetary assets and liabilities at period-end exchange rates, while nonmonetary items are remeasured at historical rates. Income and expense accounts are remeasured at the average exchange rates in effect during the period. Remeasurement adjustments are recognized in the accompanying condensed consolidated statements of operations as foreign currency transaction gains or losses in the period of occurrence. The Company incurred foreign currency transaction ~~gains~~loss of $01.35 million and foreign transaction gain of $10.71 million, respectively, in the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020. Transaction gains are included in other income (expense), net.

As our international operations grow, our risks associated with fluctuation in currency rates will become greater, and we will continue to reassess our approach to managing this risk. In addition, currency fluctuations or a weakening U.S. dollar can increase the costs of our international expansion. For our operating results and cash flows, we evaluated the effects of a 10% shift in exchange rates between those currencies and the U.S. dollar. We have determined that there would not be a material effect on our results of operations from such a shift. To date, we have not entered into any foreign currency hedging contracts, since exchange rate fluctuations have not had a material impact on our operating results and cash flows. Based on our current international structure, we do not plan on engaging in hedging activities in the near future.

Inflation Risk

We do not believe that inflation has had a material effect on our business, financial condition or results of operations. Nonetheless, if our costs were to become subject to significant inflationary pressures, we may not be able to fully offset such higher costs through price increases. Our inability or failure to do so could harm our business, financial condition and results of operations.

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ITEM 4. CONTROLS AND PROCEDURES.

Evaluation of Disclosure Controls and Procedures

Our management, with the participation of our chief executive officer and chief financial officer, evaluated the effectiveness of our disclosure controls and procedures pursuant to Rule 13a-15 under the Exchange Act. In designing and evaluating the disclosure controls and procedures, management recognizes that any controls and procedures, no matter how well designed and operated, can provide only reasonable assurance of achieving the desired control objectives. In addition, the design of disclosure controls and procedures must reflect the fact that there are resource constraints and that management is required to apply its judgment in evaluating the benefits of possible controls and procedures relative to their costs.

Based on our evaluation, our chief executive officer and chief financial officer concluded that, as of ~~March~~June 3130, 2021, our disclosure controls and procedures are designed at a reasonable assurance level and are effective to provide reasonable assurance that information we are required to disclose in reports that we file or submit under the Exchange Act is recorded, processed, summarized, and reported within the time periods specified in SEC rules and forms, and that such information is accumulated and communicated to our management, including our chief executive officer and chief financial officer, as appropriate, to allow timely decisions regarding required disclosure.

Changes in Internal Control over Financial Reporting

There were no changes in our internal control over financial reporting identified in connection with the evaluation required by Rule 13a-15(d) and 15d-15(d) of the Exchange Act that occurred during the quarter ended ~~March~~June 3130, 2021 that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting. We have not experienced any material impact to our internal control over financial reporting despite the fact that most of our employees are working remotely due to the COVID-19 pandemic. We are continually monitoring and assessing the COVID-19 situation on our internal controls to minimize the impact on their design and operating effectiveness.

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PART II. OTHER INFORMATION

ITEM 1. LEGAL PROCEEDINGS.

From time to time, we may be involved in legal proceedings and subject to claims in the ordinary course of business.

As previously disclosed in the Proxy Statement, four complaints were filed between June 3 and June 11, 2021 in the United States District Court for the Southern District of New York against Proofpoint and its directors: Stein v. Proofpoint, Inc., et al., Case No. 1:21-cv-04925 (S.D.N.Y.) (filed June 3, 2021); Ciccotelli v. Proofpoint, Inc., et al., Case No. 1:21-cv-05179 (S.D.N.Y.) (filed June 10, 2021); Ho v. Proofpoint, Inc., et al., Case No. 1:21-cv-05203 (S.D.N.Y.) (filed June 11, 2021); and Theodore v. Proofpoint, Inc., et al., Case No. 1:21-cv-05232 (S.D.N.Y.) (filed June 11, 2021). As previously disclosed in the Company’s Form 8-K, filed July 13, 2021 with the SEC, six additional complaints were filed between June 14, 2021 and June 22, 2021 by purported stockholders of Proofpoint in connection with the transactions contemplated by the Merger Agreement under the captions Andre v. Proofpoint, Inc., et al., Case No. 1:21-cv-1612 (D. Col.) (filed June 14, 2021); Finger v. Proofpoint, Inc., et al., Case No. 5:21-cv-4567 (N.D. Cal.) (filed June 14, 2021); Kent v. Proofpoint, Inc., et al., Case No. 1:21-cv-861 (D. Del.) (filed June 16, 2021); King v. Proofpoint, et al., C.A. No. 1:21-cv-05398 (S.D.N.Y.) (filed June 18, 2021); Whitfield v. Proofpoint, et al., C.A. No. 2:21-cv-02733 (E.D. Pa.) (filed June 18, 2021); and Coffman v. Proofpoint, Inc., et al., Case No. 5:21-cv-4760 (N.D. Cal.) (filed June 22, 2021). The complaints each allege that the preliminary proxy statement issued in connection with the proposed merger between Proofpoint and Thoma Bravo omitted material information which rendered the preliminary proxy statement false and misleading. Specifically, the complaints allege that the preliminary proxy statement failed to disclose material information regarding Proofpoint’s financial projections and Morgan Stanley & Co. LLC’s (“Morgan Stanley”) financial analyses. The Ciccotelli, Finger, Kent, Whitfield, and Coffman complaints also allege that the preliminary proxy statement failed to disclose past services provided by Morgan Stanley to Thoma Bravo and its affiliates. Two complaints allege that the preliminary proxy statement failed to disclose material information regarding the sales process—terms of the Company's non-disclosure agreement with Financial Sponsor A (the Andre complaint) and certain details of the go-shop process (the King complaint).

Each complaint seeks an order enjoining the proposed merger unless and until additional disclosures are issued; rescinding the proposed merger if it closes; awarding damages; awarding costs, including attorneys’ fees, expert fees and expenses; and awarding such other relief as the court deems proper. The defendants believe the complaints are without merit. It is possible additional lawsuits may be filed between the date of this Quarterly Report on Form 10-Q and consummation of the Merger.

Although the results of these proceedings and claims cannot be predicted with certainty, we do not believe the ultimate cost to resolve these matters would individually, or taken together, have a material adverse effect on our business, operating results, cash flows or financial condition. Regardless of the outcome, such proceedings can have an adverse impact on us because of defense and settlement costs, diversion of resources and other factors, and there can be no assurances that favorable outcomes will be obtained.

ITEM 1A. RISK FACTORS.

Investing in our common stock involves a high degree of risk. You should carefully consider the following risk factors, as well as the other information in this Quarterly Report on Form 10-Q, including our consolidated financial statements and the related notes and "Management’s Discussion and Analysis of Financial Condition and Results of Operations" before deciding whether to invest in shares of our common stock. The occurrence of any of the events or developments described below, or of additional risks and uncertainties not presently known to us or that we currently deem immaterial, could materially and adversely affect our business, results of operations, cash flows, financial condition and growth prospects. In such an event, the market price of our common stock could decline and you could lose all or part of your investment.

Risk Factors Summary

Our business is subject to a number of risks and uncertainties, including those risks discussed at length below. These risks include, among others, the following:

•

The Transaction, the pendency of the Transaction or our failure to complete the Transaction could have a material adverse effect on our business, results of operations, financial condition and stock price.

•

We have a history of losses, and we are unable to predict the extent of any future losses or when, if ever, we will achieve profitability in the future.

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We are unable to accurately predict the full extent to which the global COVID-19 pandemic may impact our business operations, financial performance, results of operations and stock price.

•

Weakened global economic conditions may adversely affect our industry, business and financial results.

•

Our quarterly operating results and other metrics are likely to vary significantly and be unpredictable, which could cause the trading price of our stock to decline.

•

Our customers may fail to pay us in accordance with the terms of their agreements, necessitating action by us to compel payment.

•

If we are unable to maintain high subscription renewal rates, our future revenue and operating results will be harmed.

•

If we are unable to sell additional solutions to our customers, our future revenue and operating results will be harmed.

•

If our solutions fail or are perceived to fail to protect our customers from security breaches, our brand and reputation could be harmed, which could have a material adverse effect on our business and results of operations.

•

If our customers experience data losses and breaches via our products or solutions, our brand, reputation and business could be harmed.

•

Defects or vulnerabilities in our solutions could harm our reputation, reduce the sales of our solutions and expose us to liability for losses.

•

Our software, website, hosted and internal systems may be subject to intentional disruption or penetration from external attackers or insiders that could adversely impact our reputation and future sales.

•

Our solutions may collect, filter and store customer data which may contain personal information, which raises privacy concerns and could result in us having liability or inhibit sales of our solutions.

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We operate in a highly competitive environment with large, established competitors, and our competitors may gain market share in the markets for our solutions that could adversely affect our business and cause our revenue to decline.

•

If we do not effectively expand and train our sales force, we may be unable to add new customers or increase sales to our existing customers and our business will be harmed.

•

Our sales cycle is long and unpredictable, and our sales efforts require considerable time and expense. As a result, our results are difficult to predict and may vary substantially from quarter to quarter, which may cause our operating results to fluctuate.

•

Because our long-term success depends, in part, on our ability to expand the sales of our platform to our customers located outside of the United States, our business will be increasingly susceptible to risks associated with international operations.

•

Conversion of our 2024 Notes may affect the price of our common stock and the value of the 2024 Notes.

•

Servicing our debt will require a significant amount of cash. We may not have sufficient cash flow from our business to pay our substantial debt, and we may not have the ability to raise the funds necessary to settle conversions of the 2024 Notes in cash or to repurchase the 2024 Notes upon a fundamental change, which could adversely affect our business and results of operations.

•

Share repurchases under our Repurchase Program could increase the volatility of the trading price of our common stock, could diminish our cash reserves, could occur at non-optimal prices and may not result in the most effective use of our capital.

Risks Related to Our Business and Industry

On April 25, 2021, we entered into the Merger Agreement with Parent and Merger Sub, providing for our acquisition by affiliates of funds advised by private equity investment firm Thoma Bravo, L.P. (“Thoma Bravo”). Completion of the Transaction is subject to the satisfaction of various conditions, including (1) the adoption of the Merger Agreement by a majority of the holders of the outstanding shares of our common stock, (2) the expiration or early termination of the applicable waiting period under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended, and the approval of the Merger under other applicable antitrust and foreign investment approvals, (3) the absence of any order, injunction or law prohibiting the Merger, (4) the accuracy of the other party’s representations and warranties, subject to certain materiality standards set forth in the Merger Agreement, (5) compliance in all material respects with the other party’s obligations under the Merger Agreement, and (6) no Company Material Adverse Effect (as defined in the Merger Agreement) having occurred since the date of the Merger Agreement. There is no assurance that all of the various conditions will be satisfied, or that the Transaction will be completed on the proposed terms, within the expected timeframe, or at all. Furthermore, there are additional inherent risks in the Transaction, including the risks detailed below.

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of the Transaction is subject to the satisfaction of various conditions, including (1) the approval of the Merger under applicable antitrust and foreign investment approvals, (2) the absence of any order, injunction or law prohibiting the Merger, (3) the accuracy of the other party’s representations and warranties, subject to certain materiality standards set forth in the Merger Agreement, (4) compliance in all material respects with the other party’s obligations under the Merger Agreement, and (5) no Company Material Adverse Effect (as defined in the Merger Agreement) having occurred since the date of the Merger Agreement. There is no assurance that all of the various conditions will be satisfied, or that the Transaction will be completed on the proposed terms, within the expected timeframe, or at all. Furthermore, there are additional inherent risks in the Transaction, including the risks detailed below.

During the period prior to the closing of the Transaction, our business is exposed to certain inherent risks due to the effect of the announcement or pendency of the Transaction on our business relationships, financial condition, operating results and business, including:

•

potential uncertainty in the marketplace, which could lead current and prospective customers to purchase offerings from other providers or delay purchasing from us.

•

the possibility of disruption to our business and operations, including diversion of management attention and resources.

•

the inability to attract and retain key personnel, and the possibility that our current employees could be distracted, and their productivity decline as a result, due to uncertainty regarding the Transaction.

•

the inability to pursue alternative business opportunities or make changes to our business pending the completion of the Transaction, and other restrictions on our ability to conduct our business.

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our inability to solicit other acquisition proposals during the pendency of the Transaction following the expiration of the “go-shop” period.

•

the amount of the costs, fees, expenses and charges related to the Merger Agreement and the Transaction.

•

other developments beyond our control, including, but not limited to, changes in domestic or global economic conditions that may affect the timing or success of the Transaction.

The Transaction may be delayed, and may ultimately not be completed, due to a number of factors, including:

• the failure to obtain the approval of the Merger Agreement by our stockholders.

•

the failure to obtain regulatory approvals from various governmental entities (or the imposition of any conditions, limitations or restrictions on such approvals).

• potential additional future stockholder litigation and other legal and regulatory proceedings, which could delay or prevent the Transaction.

• the failure to satisfy the other conditions to the completion of the Transaction, including the possibility that a ~~material~~Company ~~adverse~~Material ~~effect~~Adverse onEffect ~~our~~(as ~~business~~defined in the Merger Agreement) would permit Parent not to close the Transaction.

If the Transaction does not close, our business and stockholders would be exposed to additional risks, including:

•

to the extent that the current market price of our stock reflects an assumption that the Transaction will be completed, the price of our common stock could decrease if the Transaction is not completed.

• investor confidence could decline, additional stockholder litigation could be brought against us, relationships with existing and prospective customers, service providers, investors, lenders and other business partners may be adversely impacted, we may be unable to retain key personnel, and profitability may be adversely impacted due to costs incurred in connection with the pending Transaction.

• the requirement that we pay a termination fee of $368.9 million if the Merger Agreement is terminated in certain circumstances, including by the Company to enter into a superior proposal or by Parent because the Board withdraws its recommendation in favor of the Merger~~; provided that a lower fee of $123~~.~~0 million will apply with respect to a termination to enter into a superior proposal during the “go-shop” period.~~

Even if successfully completed, there are certain risks to our stockholders from the Transaction, including:

•

the amount of cash to be paid under the Merger Agreement is fixed and will not be adjusted for changes in our business, assets, liabilities, prospects, outlook, financial condition or operating results or in the event of any change in the market price of, analyst estimates of, or projections relating to, our common stock.

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the fact that receipt of the all-cash per share merger consideration under the Merger Agreement is taxable to stockholders that are treated as U.S. holders for U.S. federal income tax purposes.

•

the fact that, if the Transaction is completed, our stockholders will forego the opportunity to realize the potential long-term value of the successful execution of our current strategy as an independent company.

We have a history of losses, and we are unable to predict the extent of any future losses or when, if ever, we will achieve profitability in the future.

We have incurred net losses in every year since our inception, including net losses of $4598.32 million and $6681.89 million for the ~~three~~six months ended ~~March~~June 3130, 2021 and 2020, respectively. As a result, we had an accumulated deficit of $~~894~~947.21 million as of ~~March~~June 3130, 2021. Achieving profitability will require us to increase revenue, manage our cost structure, and avoid unanticipated liabilities. We do not expect to be profitable in the near term. Revenue growth may slow, or revenue may decline for a number of possible reasons, including slowing demand for our solutions, increasing competition, a decrease in the growth of our overall market, or if we fail for any reason to continue to capitalize on growth opportunities. Any failure by us to obtain and sustain profitability, or to continue our revenue growth, could cause the price of our common stock to decline significantly.

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We are unable to accurately predict the full extent to which the global COVID-19 pandemic may impact our business operations, financial performance, results of operations and stock price.

The COVID-19 pandemic continues to present extraordinary challenges in predicting future performance, and while we have modeled many scenarios and associated outcomes, there may be events that are more dire than we have modeled given the unique nature of this event. Although we are closely monitoring the impact of the COVID-19 pandemic and continually assess its potential effects on our business, our actual results could vary widely from our models. The extent to which our projections are affected by COVID-19 will largely depend on future developments, including the duration and spread of the outbreak, which still cannot be accurately predicted and remains uncertain. The COVID-19 pandemic or the perception of its effects could have a material adverse effect on our business, financial condition, results of operations, or cash flows.

Weakened global economic conditions may adversely affect our industry, business and financial results.

Our business depends on the overall demand for information technology and on the economic health of our current and prospective customers. Challenging economic conditions worldwide have from time to time contributed, and may continue to contribute, to slowdowns in the information technology industry, resulting in reduced demand for our solutions as a result of continued constraints on IT-related capital spending by our customers and increased price competition for our solutions. Further, any significant weakening of the economy in the United States or Europe and of the global economy, more limited availability of credit, a reduction in business confidence and activity, economic uncertainty and other difficulties, such as the COVID-19 pandemic, may affect one or more of the sectors or countries in which we sell our services. In addition, geopolitical developments, such as existing and potential trade wars and other events beyond our control, such as the COVID-19 pandemic, can increase levels of political and economic unpredictability globally and increase the volatility of global financial markets.

For example, current or potential customers have delayed and decreased and may continue to delay or decrease spending with us, or may not pay us or may delay paying us for previously performed services, given the impact that the COVID-19 pandemic has had and may continue to have on their business. Furthermore, the rate of customer terminations or service cancellations or failures to renew, which we refer to as churn, has and could also further increase as a result of the effects of the pandemic, which could include increased price competition or a reduction in customer spending. Due to restrictions on travel and in-person meetings, current or potential customers may also not be interested in taking sales meetings or cancel existing sales meetings with our sales representatives, which could materially lengthen our sales cycle and slow our sales growth. Any of these events could have an adverse effect on our business, operating results and financial position.

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Our quarterly operating results and other metrics are likely to vary significantly and be unpredictable, which could cause the trading price of our stock to decline.

Our operating results and other metrics have historically varied from period to period, and we expect that they will continue to do so as a result of a number of factors, many of which are outside of our control and may be difficult to predict, including:

•

the Transaction, the pendency of the Transaction or our failure to complete the Transaction;

•

the impact of the COVID-19 pandemic;

•

the level of demand for our solutions, including our newly-introduced solutions, and the level of perceived urgency regarding security threats and compliance requirements;

•

the timing of new subscriptions and renewals of existing subscriptions;

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the mix of solutions sold;

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the extent to which customers subscribe for additional solutions or increase the number of users;

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customer budgeting cycles and seasonal buying patterns;

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the extent to which we bring on new distributors;

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any changes in the competitive landscape of our industry, including consolidation among our competitors, customers, partners or resellers;

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timing of costs and expenses during a quarter;

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deferral of orders in anticipation of new solutions or enhancements announced by us;

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price competition;

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changes in renewal rates and terms in any quarter;

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the impact of acquisitions;

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litigation costs;

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any disruption in our sales channels or termination of our relationship with strategic channel partners;

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general economic conditions, both domestically and in our foreign markets, and related changes to currency exchange rates;

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insolvency or credit difficulties confronting our customers, affecting their ability to purchase or pay for our solutions; or

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future accounting pronouncements or changes in our accounting policies.

Any one of the factors above or the cumulative effect of some of the factors referred to above may result in significant fluctuations in our financial and other operating results, including fluctuations in our key metrics. This variability and unpredictability could result in our failing to meet the expectations of securities analysts or investors for any period. If we fail to meet or exceed such expectations for these or any other reasons, the market price of our shares could fall substantially and we could face costly lawsuits, including securities class action suits. In addition, a significant percentage of our operating expenses are fixed in nature and based on forecasted revenue and cash flow trends. Accordingly, in the event of revenue shortfalls, we are generally unable to mitigate the negative impact on margins or other operating results in the short term.

We may fail to meet or exceed the expectations of securities analysts and investors, and the market price for our common stock could decline. If one or more of the securities analysts who cover us change their recommendation regarding our stock adversely, the market price for our common stock could decline. Additionally, our stock price may be based on expectations, estimates or forecasts of our future performance that may be unrealistic or may not be achieved. Further, our stock price may be affected by financial media, including press reports and blogs.

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Our customers may fail to pay us in accordance with the terms of their agreements, necessitating action by us to compel payment.

If customers fail to pay us under the terms of our agreements, we may be adversely affected both from the inability to collect amounts due and the cost of enforcing the terms of our contracts, including through litigation. The risk of such negative effects increases with the term length of our customer arrangements. Furthermore, some of our customers have attempted to and may continue to attempt to renegotiate contracts, seek bankruptcy protection or other similar relief and fail to pay amounts due to us, or pay those amounts more slowly, either of which could adversely affect our operating results, financial position and cash flow. The recent and ongoing global COVID-19 pandemic may also increase the likelihood, frequency and magnitude of these risks.

If we are unable to maintain high subscription renewal rates, our future revenue and operating results will be harmed.

Our customers have no obligation to renew their subscriptions for our solutions after the expiration of their initial subscription period, which typically ranges from one to three years. In addition, our customers may renew for fewer subscription services or users, renew for shorter contract lengths or renew at lower prices due to competitive or other pressures. We cannot accurately predict renewal rates and our renewal rates may decline or fluctuate as a result of a number of factors, including competition, customers’ IT budgeting and spending priorities, and deteriorating general economic conditions, including as a result of the COVID-19 pandemic. If our customers do not renew their subscriptions for our solutions, our revenue would decline, and our business would suffer.

If we are unable to sell additional solutions to our customers, our future revenue and operating results will be harmed.

Our future success depends on our ability to sell additional solutions to our customers. This may require increasingly sophisticated and costly sales efforts and may not result in additional sales. In addition, the rate at which our customers purchase additional solutions depends on a number of factors, including the perceived need for additional solutions, growth in the number of end-users, and general economic conditions. If our efforts to sell additional solutions to our customers are not successful, our business may suffer.

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The threats facing our customers are constantly evolving and the techniques used by attackers to access or sabotage data change frequently. As a result, we must constantly update our solutions to respond to these threats. If we fail to update our solutions in a timely or effective manner to respond to these threats, our customers could experience security breaches. Increasingly, companies are subject to a wide variety of attacks on their networks and systems, including traditional computer hackers, malicious code (such as viruses and worms), distributed denial-of-service attacks, sophisticated attacks conducted or sponsored by nation-states, advanced persistent threat intrusions, ransomware, and theft or misuse of intellectual property or business or personal data, including by disgruntled employees, former employees or contractors. Many federal, state and foreign governments have enacted laws requiring companies to notify individuals of data security breaches involving their personal data. These mandatory disclosures regarding a security breach often lead to widespread negative publicity, and any association of us with such publicity may cause our customers to lose confidence in the effectiveness of our data security measures. Any security breach at one of our customers or even an unproven allegation of a security breach at one of our customers, could harm our reputation as a secure and trusted company and could cause the loss of customers and sales, loss of competitive advantages over our competitors, increased costs to remedy any problems and otherwise respond to any incident, regulatory investigations and enforcement actions, costly litigation, and other liability. In addition, we may incur significant costs and operational consequences of investigating, remediating, eliminating and putting in place additional tools and devices designed to prevent actual or perceived security breaches and other security incidents, as well as the costs to comply with any notification obligations resulting from any security incidents. Similarly, if a well-publicized breach of data security at a customer of any other cloud‑based data protection or archiving service provider or other major enterprise cloud services provider were to occur, there could be a loss of confidence in the cloud‑based protection and storage of sensitive data and information generally.

In addition, our solutions work in conjunction with a variety of other elements in customers’ IT and security infrastructure, and we may receive blame and negative publicity for a security breach that may have been the result of the failure of one of the other elements not provided by us. The occurrence of a breach, whether or not caused by our solutions, or allegations of a breach, even if such allegations turn out to be untrue, could delay or reduce market acceptance of our solutions and have an adverse effect on our business and financial performance. In addition, any revisions to our solutions that we believe may be necessary or appropriate in connection with any such breach may cause us to incur significant expenses. We cannot assure you that any of our efforts to manage this risk, including adoption of a comprehensive incident response plan and process for detecting, mitigating, and investigating security incidents that we test through table-top exercises, testing of our security protocols through additional techniques, such as penetration testing, debriefing after security incidents, to improve our security and responses, and regular briefing of our directors and officers on our cybersecurity risks, preparedness, and management, will be effective in protecting us from such attacks. Any of these events could have material adverse effects on our brand and reputation, which could harm our business, financial condition, and operating results.

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response plan and process for detecting, mitigating, and investigating security incidents that we test through table-top exercises, testing of our security protocols through additional techniques, such as penetration testing, debriefing after security incidents, to improve our security and responses, and regular briefing of our directors and officers on our cybersecurity risks, preparedness, and management, will be effective in protecting us from such attacks. Any of these events could have material adverse effects on our brand and reputation, which could harm our business, financial condition, and operating results.

If our customers experience data losses and breaches via our products or solutions, our brand, reputation and business could be harmed.

Our customers rely on our archiving and other solutions to protect, transfer or store their corporate data, which may include financial records, credit card information, business information, health information, other personally identifiable information or other sensitive personal information. A breach of our network security and systems or other events that cause the loss or public disclosure of, or access by third parties to, our customers’ stored files or data could have serious negative consequences for our business, including possible fines, penalties and damages, reduced demand for our solutions, an unwillingness of our customers to use our solutions, harm to our brand and reputation, and time-consuming and expensive litigation. The techniques used to obtain unauthorized access, disable or degrade service, or sabotage systems change frequently, often are not recognized until launched against a target, and may originate from less regulated or remote areas around the world. As a result, we may be unable to proactively prevent these techniques, implement adequate preventative or reactionary measures, or enforce the laws and regulations that govern such activities. In addition, because of the large amount of data that we collect and manage, it is possible that hardware failures, insider errors or malfeasance or errors in our systems could result in data loss or corruption, or cause the information that we collect to be incomplete or contain inaccuracies that our customers regard as significant. If our customers experience any data loss, or any data corruption or inaccuracies, whether caused by security breaches or otherwise, our brand, reputation and business would be harmed.

Our insurance may be inadequate or may not be available in the future on acceptable terms, or at all. In addition, our policy may not cover any claim against us for loss of data or other indirect or consequential damages. Defending a suit based on any data loss or system disruption, regardless of its merit, could be costly and divert management’s attention.

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Defects or vulnerabilities in our solutions could harm our reputation, reduce the sales of our solutions and expose us to liability for losses.

Because our solutions are complex, undetected errors, failures or bugs may occur, especially when solutions are first introduced or when new versions or updates are released, or when we introduce an acquired company’s products of services, despite our efforts to test those solutions and enhancements prior to release. This includes not only vulnerabilities that are specific to our solutions, but also vulnerabilities that impact the third-party or open source software or services that we use or the hardware that we rely on for our solutions. Additionally, we may be impacted by the evaluation of the security of our services by third party security scoring companies whether those evaluations are accurate or not. We may not be able to correct defects, errors, vulnerabilities or failures promptly, or to correct inaccuracies in perceptions about these matters at all.

Any defects, errors, vulnerabilities or failures in our solutions could result in:

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expenditure of significant financial and development resources in efforts to analyze, correct, eliminate or work around errors or defects or to address and eliminate vulnerabilities;

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loss of existing or potential partners or customers or loss of customer confidence;

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loss or disclosure of our customers’ confidential information, or the inability to access such information;

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loss of our proprietary technology;

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our solutions being susceptible to hacking or electronic break-ins or otherwise failing to secure data;

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delayed or lost revenue;

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delay or failure to attain market acceptance;

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lost market share;

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negative publicity, which could harm our reputation; or

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litigation, regulatory inquiries or investigations that would be costly and harm our reputation.

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Limitation of liability provisions in our standard terms and conditions and our other agreements may not adequately or effectively protect us from any claims related to defects, errors, vulnerabilities or failures in our solutions, including as a result of federal, state or local laws or ordinances or unfavorable judicial decisions in the United States or other countries.

We could be a target of attacks specifically designed to impede the performance of our solutions, redirect users to malicious sites, harm our reputation and brand, or misappropriate our or our customers’ proprietary information. Similarly, experienced computer hackers may attempt to penetrate our network or other security or the security of our website or other hosted or internal systems or to trick our employees into taking actions that compromise our security (such as via phishing or business email compromise attacks) in order to misappropriate proprietary information and/or cause interruptions of our services and/or expose perceived security vulnerabilities. It is also possible that systems may be disrupted or our sensitive information or the information of our customers might be exposed due to malfeasance or errors by employees or contractors. Because the techniques used by attackers to access or sabotage networks and compromise our systems and information change frequently and may not be recognized until launched against a target, we may be unable to anticipate these techniques. If an actual or perceived breach of network security occurs as a result of third-party action, including cyber-attacks or other intentional misconduct by computer hackers conducted or sponsored by nation-states, error or malfeasance by insiders, or otherwise, it could adversely affect the market perception of our company and our solutions, may expose us to the loss of information, litigation and possible liability, and could cause a loss in revenue due to reputational or brand damage and customer churn. In addition, such a security breach could impair our ability to operate our business, including our ability to provide support services to our customers.

Many federal, state and foreign government bodies and agencies have adopted or are considering adopting laws and regulations regarding the collection, use, and disclosure of personal information. Because many of the features of our solutions use, store, and report on customer data which may contain personal information from our customers, any inability to adequately address privacy concerns, or comply with applicable privacy laws, regulations and policies could, even if unfounded, result in liability to us, damage to our reputation, loss of sales, and harm to our business. Furthermore, the costs of compliance with, and other burdens imposed by, such laws, regulations and policies that are applicable to the businesses of our customers may limit the use and adoption of our solutions and reduce overall demand for them. Privacy concerns, whether or not valid, may inhibit market adoption of our solutions. For example, in the United States regulations such as the Gramm‑Leach‑Bliley Act, which protects and restricts the use of consumer credit and financial information, and HIPAA which regulates the use and disclosure of personal health information, impose significant security and data protection requirements and obligations on businesses that may affect the use and adoption of our solutions. Similarly, we hold a FedRAMP authorization without which we would not be able to provide services and products to certain US federal entities.

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unfounded, result in liability to us, damage to our reputation, loss of sales, and harm to our business. Furthermore, the costs of compliance with, and other burdens imposed by, such laws, regulations and policies that are applicable to the businesses of our customers may limit the use and adoption of our solutions and reduce overall demand for them. Privacy concerns, whether or not valid, may inhibit market adoption of our solutions. For example, in the United States regulations such as the Gramm‑Leach‑Bliley Act, which protects and restricts the use of consumer credit and financial information, and HIPAA which regulates the use and disclosure of personal health information, impose significant security and data protection requirements and obligations on businesses that may affect the use and adoption of our solutions. Similarly, we hold a FedRAMP authorization without which we would not be able to provide services and products to certain US federal entities.

In the past we have relied on U.S.-European Union Frameworks for transatlantic data flows such as the EU-U.S. Privacy Shield, for which we self-certified under the EU-U.S. Privacy Shield framework on October 5, 2016. However, on July 16, 2020, the Court of Justice of the EU issued a decision invalidating outright the EU-U.S. Privacy Shield framework and as a result, we no longer rely on that framework. We currently rely on Standard Contractual Clauses (“SCCs”) authorized by the EU’s Data Protection Directive of 1995 for transatlantic data flows, including successor versions soon to be finalized and issued by the European Commission. Additionally, the EU’s General Data Protection Regulation, began to be enforced on May 25, 2018, and carries with it significantly increased responsibilities and potential penalties for companies that process EU personal data. We have seen increased customer attention surrounding EU Data Privacy. Furthermore, outside of the EU, we continue to see increased regulation of data privacy and security, including the adoption of more stringent subject matter specific state laws (such as the New York Department of Financial Services’ Cybersecurity Regulation, the California Consumer Privacy Act of 2018 that became effective January 1, 2020, and the new California Privacy Rights Act), national laws regulating the collection and use of data, and security and data breach obligations. The uncertainty and changes in the requirements of multiple jurisdictions may increase the cost of compliance, delay or reduce demand for our services, restrict our ability to offer services in certain locations, impact our customers’ ability to deploy our solutions in certain jurisdictions, or subject us to sanctions, by national data protection regulators, all of which could harm our business, financial condition and results of operations.

The regulatory framework for privacy issues is evolving worldwide, and various government and consumer agencies and public advocacy groups have called for new regulation and changes in industry practices. It is possible that new laws and regulations will be adopted in the United States and internationally, or existing laws and regulations may be interpreted in new ways, that would affect our business. Complying with any new regulatory requirements could force us to incur ~~substantial costs or require us to change our business practices in a manner that could reduce our revenue or compromise our ability to effectively pursue our growth strategy.~~

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substantial costs or require us to change our business practices in a manner that could reduce our revenue or compromise our ability to effectively pursue our growth strategy.

Any failure or perceived failure to comply with laws and regulations or loss of certifications such as the FedRAMP authorization may result in proceedings or actions against us by government entities or others, or could cause us to lose users and customers, which could potentially have an adverse effect on our business.

Our traditional competitors include security‑focused software vendors, such as Broadcom Inc. and Cisco Systems, Inc., which offer software products that directly compete with our solutions. In addition to competing with these vendors directly for sales to customers, we compete with them for the opportunity to have our solutions bundled with the product offerings of our strategic partners. Our competitors could gain market share from us if any of these partners replace our solutions with the products of our competitors or if these partners more actively promote our competitors’ products over our solutions. In addition, software vendors who have bundled our solutions with theirs may choose to bundle their software with their own or other vendors’ software, or may limit our access to standard product interfaces and inhibit our ability to develop solutions for their platform.

We also face competition from large technology companies, such as Broadcom Inc., Cisco Systems, Inc., Google Inc., Micro Focus International plc and Microsoft Corporation. These companies are increasingly developing and incorporating into their products features that compete on various levels with our solutions. Our competitive position could be adversely affected to the extent that our customers perceive that the functionality incorporated into these products would replace the need for our solutions or that buying from one vendor would provide them with increased leverage and purchasing power and a better customer experience. We also face competition from independent security vendors such as FireEye, Inc. that offer network security products and many smaller companies like Mimecast Ltd. that specialize in particular segments of the markets in which we compete.

Many of our competitors have greater financial, technical, sales, marketing or other resources than we do and consequently may have the ability to influence our customers to purchase their products instead of ours. Further consolidation within our industry or other changes in the competitive environment could also result in larger competitors that compete with us on several levels. In addition, acquisitions of smaller companies by large technology companies that specialize in particular segments of the markets in which we compete would result in increased competition from these large technology companies. If we are unsuccessful in responding to our competitors or to changing technological and customer demands, our competitive position and financial results could be adversely affected.

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us on several levels. In addition, acquisitions of smaller companies by large technology companies that specialize in particular segments of the markets in which we compete would result in increased competition from these large technology companies. If we are unsuccessful in responding to our competitors or to changing technological and customer demands, our competitive position and financial results could be adversely affected.

If we do not effectively expand and train our sales force, we may be unable to add new customers or increase sales to our existing customers and our business will be harmed.

We continue to be substantially dependent on our sales force to obtain new customers and to sell additional solutions to our existing customers. We believe that there is significant competition for sales personnel with the skills and technical knowledge that we require. Our ability to achieve significant revenue growth will depend, in large part, on our success in recruiting, training and retaining sufficient numbers of sales personnel. New hires require significant training and may take significant time before they achieve full productivity, a period which may be prolonged due to the remote working arrangements we have adopted due to the COVID-19 pandemic. Our recent hires and planned hires may not become as productive as we expect, and we may be unable to hire or retain sufficient numbers of qualified individuals in the markets where we do business or plan to do business. If we are unable to hire and train sufficient numbers of effective sales personnel, or the sales personnel are not successful in obtaining new customers or increasing sales to our existing customer base, our business will be harmed.

We sell our security and compliance offerings primarily to enterprise IT departments that are managing a growing set of user and compliance demands, which has increased the complexity of customer requirements to be met and confirmed in the sales cycle. Increasingly, we have found that security, legal and compliance departments are involved in testing, evaluating and finally approving purchases, which has also made the sales cycle longer and less predictable. We may not be able to accurately predict or forecast the timing of sales, which makes our future revenue difficult to predict and could cause our results to vary significantly. In addition, we might devote substantial time and effort to a particular unsuccessful sales ~~effort, and as a result we could lose other sales opportunities or incur expenses that are not offset by an increase in revenue, which could harm our business.~~

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effort, and as a result we could lose other sales opportunities or incur expenses that are not offset by an increase in revenue, which could harm our business.

One key element of our growth strategy is to develop a worldwide customer base and expand our operations worldwide, such as by adding employees, offices and customers internationally, particularly in Europe and Asia.

Operating in international markets requires significant resources and management attention and will subject us to regulatory, economic, political and competitive risks and competition that are different from those in the United States.

In addition, our international operations may fail to succeed due to other risks inherent in operating businesses internationally, including:

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fluctuations in currency exchange rates, including as a result of volatile market conditions arising from the COVID-19 pandemic, which may cause our revenues and operating results to differ materially from expectations;

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our lack of familiarity with commercial and social norms and customs in other countries which may adversely affect our ability to recruit, retain and manage employees in these countries;

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difficulties and costs associated with staffing and managing foreign operations;

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the potential diversion of management’s attention to oversee and direct operations that are geographically distant from our U.S. headquarters;

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compliance with multiple, conflicting and changing governmental laws and regulations, including employment, tax, privacy and data protection laws and regulations;

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legal systems in which our ability to enforce and protect our rights may be different or less effective than in the United States, including more limited protection for intellectual property rights in some countries;

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immaturity of compliance regulations in other jurisdictions, which may lower demand for our solutions;

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greater difficulty with payment collections and longer payment cycles;

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higher employee costs and difficulty terminating non-performing employees;

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differences in workplace cultures;

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the need to adapt our solutions for specific countries;

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our ability to comply with differing technical and certification requirements outside the United States;

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tariffs, export controls and other non-tariff barriers such as quotas and local content rules;

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uncertainties related to the United Kingdom’s withdrawal from the European Union (“Brexit”) and its impact on our customers, data protection regulations and our employees and their ability to emigrate and travel to and from the United Kingdom;

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adverse tax consequences;

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restrictions on the transfer of funds;

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anti-bribery compliance by us or our partners, including under the Foreign Corrupt Practices Act and similar laws of other jurisdictions; and

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new and different sources of competition.

In addition, the prior U.S. administration has instituted or proposed changes to foreign trade policy including the negotiation or termination of trade agreements, the imposition of tariffs on products imported from certain countries, economic sanctions on individuals, corporations or countries and other government regulations affecting trade between the United States and other countries in which we do business. As a result, certain foreign governments have instituted or are considering imposing trade sanctions on certain U.S. manufactured goods. The escalation of protectionist or retaliatory trade measures in either the United States or any other countries in which we do business, such as a change in tariff structures, export compliance or other trade policies, may increase the cost of, or otherwise interfere with, conducting our business.

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measures in either the United States or any other countries in which we do business, such as a change in tariff structures, export compliance or other trade policies, may increase the cost of, or otherwise interfere with, conducting our business.

Our failure to manage any of these risks successfully could harm our existing and future international operations and seriously impair our overall business.

If we are unable to enhance our existing solutions and develop new solutions, our growth will be harmed, and we may not be able to achieve profitability.

Our ability to attract new customers and increase revenue from existing customers will depend in large part on our ability to enhance and improve our existing solutions and to introduce new solutions. The success of any enhancement or new solution depends on several factors, including the timely completion, introduction and market acceptance of the enhancement or solution. Any new enhancement or solution we develop or acquire may not be introduced in a timely or cost-effective manner and may not achieve the broad market acceptance necessary to generate significant revenue. If we are unable to successfully develop or acquire new solutions or enhance our existing solutions to meet customer requirements, we may not grow as expected and we may not achieve profitability.

We cannot be certain that our development activities will be successful or that we will not incur delays or cost overruns. Furthermore, we may not have sufficient financial resources to identify and develop new technologies and bring enhancements or new solutions to market in a timely and cost-effective manner. New technologies and enhancements could be delayed or cost more than we expect, and we cannot ensure that any of these solutions will be commercially successful if and when they are introduced.

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If we are unable to cost-effectively scale or adapt our existing architecture to accommodate increased traffic, technological advances or changing customer requirements, our operating results could be harmed.

As our customer base grows, the number of users accessing our solutions over the Internet will correspondingly increase. Increased traffic could result in slow access speeds and response times. Since our customer agreements often include service availability commitments, slow speeds or our failure to accommodate increased traffic could result in breaches of our service level agreements or obligate us to issue service credits. In addition, the market for our solutions is characterized by rapid technological advances and changes in customer and regulatory requirements. In order to accommodate increased traffic and respond to technological advances and evolving customer and regulatory requirements, we expect that we will be required to make future investments in our network architecture. If we do not implement future upgrades to our network architecture cost-effectively, or if we experience prolonged delays or unforeseen difficulties in connection with upgrading our network architecture, our service quality may suffer, and our operating results could be harmed.

If we fail to manage our sales and distribution channels effectively or if our partners choose not to market and sell our solutions to their customers, our operating results could be adversely affected.

We have derived and anticipate that in the future we will continue to derive a substantial portion of the sales of our solutions through channel partners. In order to scale our channel program to support growth in our business, it is important that we continue to help our partners enhance their ability to independently sell and deploy our solutions. We may be unable to continue to successfully expand and improve the effectiveness of our channel sales program.

Our agreements with our channel partners are generally non-exclusive and some of our channel partners have entered, and may continue to enter, into strategic relationships with our competitors or are competitors themselves. Further, many of our channel partners have multiple strategic relationships and they may not regard us as significant for their businesses. Our channel partners may terminate their respective relationships with us with limited or no notice and with limited or no penalty, pursue other partnerships or relationships, or attempt to develop or acquire products or services that compete with our solutions. Our partners also may impair our ability to enter into other desirable strategic relationships. If our channel partners do not effectively market and sell our solutions, if they choose to place greater emphasis on products of their own or those offered by our competitors, or if they fail to meet the needs of our customers, our ability to grow our business and sell our solutions may be adversely affected. Similarly, the loss of a substantial number of our channel partners, and our possible inability to replace them, the failure to recruit additional channel partners, any reduction or delay in their sales of our solutions, or any conflicts between channel sales and our direct sales and marketing activities could materially and adversely affect our results of operations.

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Because we recognize revenue from subscriptions over the term of the relevant service period, decreases or increases in sales are not immediately reflected in full in our operating results.

We recognize revenue from subscriptions over the term of the relevant service period, which typically range from one to three years, with some up to five years. As a result, most of our quarterly revenue from subscriptions results from agreements entered into during previous quarters. Consequently, a shortfall in demand for our solutions in any quarter may not significantly reduce our subscription revenue for that quarter, but could negatively affect subscription revenue in future quarters. We may be unable to adjust our cost structure to compensate for this potential shortfall in subscription revenue. Accordingly, the effect of significant downturns in sales of subscriptions may not be fully reflected in our results of operations until future periods. Our subscription model also makes it difficult for us to rapidly increase our subscription revenue through additional sales in any period, as subscription revenue must be recognized over the term of the contract.

Any interruptions or delays in services provided through our internal operations or by third-parties, including data center hosting facilities, network service providers, cloud computing platform providers and other hardware and software vendors, or from our inability to adequately plan for and manage service interruptions or infrastructure capacity requirements, could impair the delivery of our services and harm our business.

Our business operations are subject to interruption by natural disasters, fire, power shortages, pandemics (including the ongoing COVID-19 pandemic) and other events beyond our control. We rely on a number of third-party providers for data center hosting facilities, equipment, maintenance and other services, and the loss of, or problems with, one or more of these providers or our internal operations and infrastructure, including any potential disruptions due to significantly increased global demand on certain cloud-based systems during the COVID-19 pandemic, may impact our ability to properly maintain and repair our systems, thereby causing us to lose customers.

We currently serve our customers from third‑party data center facilities and resources located in the United States, Canada, Australia and Europe. We also rely on bandwidth providers, Internet service providers, mobile networks and other third-party IT service providers to operate our business and to deliver our solutions. Any damage to, or failure or disruption of, the systems of our third‑party providers could result in interruptions to our service. If for any reason our arrangement with one or more of our data centers is terminated, we could experience additional expense in arranging for new facilities and support. Our data center facilities providers have no obligations to renew their agreements with us on commercially reasonable terms, or at all. If we are unable to renew our agreements with the facilities providers on commercially reasonable terms or if in the future we add additional data center facility providers, we may experience costs or downtime in connection with the transfer to, or the addition of, new data center facilities. In addition, the failure of our data centers to meet our capacity requirements could result in interruptions in the availability of our solutions, impair the functionality of our solutions or impede our ability to scale our operations. As we continue to add data centers, restructure our data management plans, and increase capacity in existing and future data centers, we may move or transfer our data and our customers’ data. Despite precautions taken during such processes and procedures, any unsuccessful data transfers may impair the delivery of our service, and we may experience costs or downtime in connection with the transfer of data to other facilities. Similarly, some of our solutions’ features run or depend on IT services run by third parties, such as data feeds or public clouds, such as Amazon Web Services and Google Cloud, and an extended failure of such services might materially and adversely impact our ability to provide our services to our customers. Furthermore, some of our sales and business operations, such as CRM and billing and invoicing depend in part on third-party IT service providers and if those services were to be unavailable for extended periods of time it might materially and adversely affect our ability to operate.

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third-party IT service providers to operate our business and to deliver our solutions. Any damage to, or failure or disruption of, the systems of our third‑party providers could result in interruptions to our service. If for any reason our arrangement with one or more of our data centers is terminated, we could experience additional expense in arranging for new facilities and support. Our data center facilities providers have no obligations to renew their agreements with us on commercially reasonable terms, or at all. If we are unable to renew our agreements with the facilities providers on commercially reasonable terms or if in the future we add additional data center facility providers, we may experience costs or downtime in connection with the transfer to, or the addition of, new data center facilities. In addition, the failure of our data centers to meet our capacity requirements could result in interruptions in the availability of our solutions, impair the functionality of our solutions or impede our ability to scale our operations. As we continue to add data centers, restructure our data management plans, and increase capacity in existing and future data centers, we may move or transfer our data and our customers’ data. Despite precautions taken during such processes and procedures, any unsuccessful data transfers may impair the delivery of our service, and we may experience costs or downtime in connection with the transfer of data to other facilities. Similarly, some of our solutions’ features run or depend on IT services run by third parties, such as data feeds or public clouds, such as Amazon Web Services and Google Cloud, and an extended failure of such services might materially and adversely impact our ability to provide our services to our customers. Furthermore, some of our sales and business operations, such as CRM and billing and invoicing depend in part on third-party IT service providers and if those services were to be unavailable for extended periods of time it might materially and adversely affect our ability to operate.

We also depend on access to the Internet through third‑party bandwidth providers to operate our business. If we lose the services of one or more of our bandwidth providers, or if these providers experience outages, for any reason, we could experience disruption in delivering our solutions or we could be required to retain the services of a replacement bandwidth provider. Our business also depends on our customers having high-speed access to the Internet. Any Internet outages or delays could adversely affect our ability to provide our solutions to our customers.

Our operations rely heavily on the availability of electricity, which also comes from third-party providers. If we or the third-party data center facilities that we use to deliver our services were to experience a major power outage or if the cost of electricity were to increase significantly, our operations and financial results could be harmed. If we or our third‑party data centers were to experience a major power outage, we or they would have to rely on back-up generators, which might not work properly or might not provide an adequate power supply during a major power outage. Such a power outage could result in a significant disruption of our business.

For example, the COVID-19 pandemic and its adverse effects have become more prevalent in the locations where we conduct business and as a result, we have begun to experience more pronounced disruptions in our daily internal operations, including the closures of our physical domestic and international offices to promote the safety and security of our employees and to support the communities in which we operate. We have instituted remote working arrangements for employees where practicable, resulting in potential latent inefficiencies that may impact our operations.

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Although we maintain crisis management and disaster response plans, including our business continuity plan, such events could make it difficult or impossible for us to deliver our services to our customers, could lead to lengthy interruptions in our service, and could decrease demand for our services. The occurrence of an extended interruption of our or third‑party services for any reason could result in lengthy interruptions in our services or in the delivery of customers’ email and require us to provide service credits, refunds, indemnification payments or other payments to our customers, and could also result in the loss of customers. Additionally, any such system failures or outages could compromise our ability to conduct business or delay our financial reporting, which could materially affect our operating results and financial condition.

Any failure to offer or the inability of our customers to access our high-quality technical support services may adversely affect our relationships with our customers and harm our financial results.

Once our solutions are deployed, our customers depend on accessing our support organization to resolve any technical issues relating to our solutions, which may be impaired by interruptions caused by natural disasters, fire, power shortages, pandemics (including the ongoing COVID-19 pandemic) and other events beyond our control. In addition, our sales process is highly dependent on our solutions and business reputation and on strong recommendations from our existing customers. Any failure to maintain or the inability of our customers to access our high-quality technical support, or a market perception that we do not maintain high-quality support or the inability of our customers to access our high-quality support, could harm our reputation, adversely affect our ability to sell our solutions to existing and prospective customers, and harm our business, operating results and financial condition.

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We offer technical support services with many of our solutions. We may be unable to respond quickly enough to accommodate short-term increases in customer demand for support services. We also may be unable to modify the format of our support services to compete with changes in support services provided by competitors. Increased customer demand for these services, without corresponding revenue, could increase costs and adversely affect our operating results.

We have outsourced a substantial portion of our worldwide customer support functions to third‑party service providers. If these companies experience financial difficulties, do not maintain sufficiently skilled workers and resources to satisfy our contracts, or otherwise fail to perform at a sufficient level, the level of support services to our customers may be significantly disrupted, which could materially harm our reputation and our relationships with these customers.

If we fail to develop or protect our brand, our business may be harmed.

We believe that developing and maintaining awareness and integrity of our company and our brand are important to achieving widespread acceptance of our existing and future offerings and are important elements in attracting new customers. We believe that the importance of brand recognition will increase as competition in our market further intensifies. Successful promotion of our brand will depend on the effectiveness of our marketing efforts and on our ability to provide reliable and useful solutions at competitive prices. We plan to continue investing substantial resources to promote our brand, both domestically and internationally, but there is no guarantee that our brand development strategies will enhance the recognition of our brand. Some of our existing and potential competitors have well-established brands with greater recognition than we have. If our efforts to promote and maintain our brand are not successful, our operating results and our ability to attract and retain customers may be adversely affected. In addition, even if our brand recognition and loyalty increase, this may not result in increased use of our solutions or higher revenue.

In addition, independent industry analysts often provide reviews of our solutions, as well as those of our competitors, and perception of our solutions in the marketplace may be significantly influenced by these reviews. We have no control over what these industry analysts report, and because industry analysts may influence current and potential customers, our brand could be harmed if they do not provide a positive review of our solutions or view us as a market leader.

The steps we have taken to protect our intellectual property rights may not be adequate.

We rely on a combination of contractual rights, trademarks, trade secrets, patents and copyrights to establish and protect our intellectual property rights. These offer only limited protection, however, and the steps we have taken to protect our proprietary technology may not deter its misuse, theft or misappropriation. Any of our patents, copyrights, trademarks or other intellectual property rights may be challenged by others or invalidated through administrative process or litigation. Competitors may independently develop technologies or products that are substantially equivalent or superior to our solutions or that inappropriately incorporate our proprietary technology into their products. Competitors may hire our former employees who may misappropriate our proprietary technology or misuse our confidential information. Although we rely in part upon confidentiality agreements with our employees, consultants and other third parties to protect our trade secrets and other confidential information, those agreements may not effectively prevent disclosure of trade secrets and other confidential information and may not provide an adequate remedy in the event of misappropriation of trade secrets or unauthorized disclosure of confidential information. In addition, others may independently discover our trade secrets and confidential information, and in such cases, we could not assert any trade secret rights against such parties.

We might be required to spend significant resources to monitor and protect our intellectual property rights. We may initiate claims or litigation against third parties for infringement of our intellectual property rights or misappropriation of our trade secrets, or to establish the validity of our intellectual property rights. Any litigation, whether or not it is resolved in our favor, could result in significant expense to us and divert the efforts of our technical and management personnel, which may adversely affect our business, operating results and financial condition. Certain jurisdictions may not provide adequate legal infrastructure for effective protection of our intellectual property rights. Changing legal interpretations of liability for unauthorized use of our solutions or lessened sensitivity by corporate, government or institutional users to refraining from intellectual property piracy or other infringements of intellectual property could also harm our business.55

Our issued patents may not provide us with any competitive advantages or may be challenged by third parties, and our patent applications may never be granted at all. It is possible that innovations for which we seek patent protection may not be protectable. Additionally, the process of obtaining patent protection is expensive and time consuming, and we may not be able to prosecute all necessary or desirable patent applications at a reasonable cost or in a timely manner. Given the cost, effort, risks and downside of obtaining patent protection, including the requirement to ultimately disclose the invention to the public, we may not choose to seek patent protection for certain innovations. However, such patent protection could later prove to be important to our business. Even if issued, there can be no assurance that any patents will have the coverage originally sought or adequately protect our intellectual property, as the legal standards relating to the validity, enforceability and scope of protection of patent and other intellectual property rights are uncertain. Any patents that are issued may be invalidated or otherwise limited, or may lapse or may be abandoned, enabling other companies to better develop products that

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~~compete~~We ~~with~~might be required to spend significant resources to monitor and protect our ~~solutions~~intellectual property rights. We may initiate claims or litigation against third parties for infringement of our intellectual property rights or misappropriation of our trade secrets, ~~which~~or to establish the validity of our intellectual property rights. Any litigation, whether or not it is resolved in our favor, could ~~adversely~~result ~~affect~~in significant expense to us and divert the efforts of our ~~competitive~~technical ~~business~~and ~~position~~management personnel, which may adversely affect our business, ~~prospects~~operating results and financial condition. Certain jurisdictions may not provide adequate legal infrastructure for effective protection of our intellectual property rights. Changing legal interpretations of liability for unauthorized use of our solutions or lessened sensitivity by corporate, government or institutional users to refraining from intellectual property piracy or other infringements of intellectual property could also harm our business.

We cannot assure you that the measures we have taken to protect our intellectual property will adequately protect us, and any failure to protect our intellectual property could harm our business.

Third parties claiming that we infringe their intellectual property rights could cause us to incur significant legal expenses and prevent us from selling our solutions.

Companies and individuals in the software and technology industries, including some of our current and potential competitors, own large numbers of patents, copyrights, trademarks and trade secrets and frequently enter into litigation based on allegations of infringement, misappropriation or other violations of intellectual property rights. In addition, many of these third parties have the capability to dedicate substantially greater resources to enforce their intellectual property rights and to defend claims that may be brought against them. The litigation may involve patent holding companies or other adverse patent owners who have no relevant product revenue and against whom our potential patents may provide little or no deterrence. We have received, and may in the future receive, notices that claim we have infringed, misappropriated or otherwise violated other parties’ intellectual property rights. We have been involved in litigation involving such allegations of infringement. To the extent we gain greater visibility, we could face a higher risk of being the subject of intellectual property infringement claims, which is not uncommon with respect to software technologies in general and information security technology in particular. There may be third‑party intellectual property rights, including issued or pending patents that cover significant aspects of our technologies or business methods. Any intellectual property claims, with or without merit, could be very time consuming, could be expensive to settle or litigate and could divert our management’s attention and other resources. These claims could also subject us to significant liability for damages, potentially including treble damages if we are found to have willfully infringed patents or copyrights. These claims could also result in our having to stop using technology found to be in violation of a third-party’s rights. We might be required to seek a license for the intellectual property, which may not be available on reasonable terms or at all. Even if a license were available, we could be required to pay significant royalties, which would increase our operating expenses. As a result, we may be required to develop alternative non-infringing technology, which could require significant effort and expense. If we cannot license or develop technology for any infringing aspect of our business, we would be forced to limit or stop sales of one or more of our solutions or features of our solutions and may be unable to compete effectively. Any of these results would harm our business, operating results and financial condition.

In addition, our agreements with customers and channel partners include indemnification provisions under which we agree to indemnify them for losses suffered or incurred as a result of claims of intellectual property infringement and, in some cases, for damages caused by us to property or persons. Large indemnity payments could harm our business, operating results and financial condition.

We rely on technology and intellectual property licensed from other parties, the failure or loss of which could increase our costs and delay or prevent the delivery of our solutions.

We utilize various types of software and other technology, as well as intellectual property rights, licensed from unaffiliated third parties in order to provide certain elements of our solutions. Any errors or defects in any third‑party technology could result in errors in our solutions that could harm our business. In addition, licensed technology and intellectual property rights may not continue to be available on commercially reasonable terms, or at all. While we believe that there are currently adequate replacements for the third‑party technology we use, any loss of the right to use any of this technology on commercially reasonable terms, or at all, could result in delays in producing or delivering our solutions until equivalent technology is identified and integrated, which delays could harm our business. In this situation we would be required to either redesign our solutions to function with software available from other parties or to develop these components ourselves, which would result in increased costs. Furthermore, we might be forced to limit the features available in our current or future solutions. If we fail to maintain or renegotiate any of these technology or intellectual property licenses, we could face significant delays and diversion of resources in attempting to develop similar or replacement technology, or to license and integrate a functional equivalent of the technology.

~~Some of our solutions contain “open source” software, and any failure to comply with the terms of one or more of these open source licenses could negatively affect our business.~~56

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~~certain~~Some ~~open source licenses, we could be required to release the source code~~ of our ~~proprietary~~solutions ~~software,~~contain ~~and to make our proprietary software available under~~ “open source” ~~licenses, if we combine our proprietary~~ software ~~with open source software in a certain manner. In the event that portions of our proprietary software are determined to be subject to an open source license~~, weand ~~could~~any befailure ~~required~~ to ~~publicly~~comply ~~release~~with the ~~affected~~terms ~~portions~~ of ~~our~~one ~~source code, re-engineer all~~ or amore ~~portion~~ of our technologies, or otherwise be limited in the licensing of our technologies, each of which could reduce or eliminate the value of our technologies and solutions. In addition to risks related to license requirements, usage of open source software can lead to greater risks than use of third-party commercial software, as open source licensors generally do not provide warranties or controls on the origin of the software. We have established processes to help alleviate these ~~risks, including a review process for screening requests from our development organizations for the use of~~ open source ~~software,~~licenses but we cannot be sure that all open source software is submitted for approval prior to use in our solutions, that our programmers have not incorporated open source software into our proprietary solutions and technologies or that they will not do so in the future. In addition, many of the risks associated with usage of open source software cannot be eliminated, and could, ~~if not properly addressed,~~ negatively affect our business.

Some of our solutions are distributed with software licensed by its authors or other third parties under so-called “open source” licenses, which may include, by way of example, the GNU General Public License, or GPL, and the Apache License. Some of these licenses contain requirements that we make available source code for modifications or derivative works we create based upon the open source software, and that we license such modifications or derivative works under the terms of a particular open source license or other license granting third parties certain rights of further use. By the terms of certain open source licenses, we could be required to release the source code of our proprietary software, and to make our proprietary software available under open source licenses, if we combine our proprietary software with open source software in a certain manner. In the event that portions of our proprietary software are determined to be subject to an open source license, we could be required to publicly release the affected portions of our source code, re-engineer all or a portion of our technologies, or otherwise be limited in the licensing of our technologies, each of which could reduce or eliminate the value of our technologies and solutions. In addition to risks related to license requirements, usage of open source software can lead to greater risks than use of third-party commercial software, as open source licensors generally do not provide warranties or controls on the origin of the software. We have established processes to help alleviate these risks, including a review process for screening requests from our development organizations for the use of open source software, but we cannot be sure that all open source software is submitted for approval prior to use in our solutions, that our programmers have not incorporated open source software into our proprietary solutions and technologies or that they will not do so in the future. In addition, many of the risks associated with usage of open source software cannot be eliminated, and could, if not properly addressed, negatively affect our business.

Governmental regulations affecting the export of certain of our solutions could negatively affect our business.

Some of our products are subject to U.S. export controls, and we incorporate encryption technology into certain of our products. These encryption products and the underlying technology may be exported outside the United States only with the required export authorizations, including by license, a license exception or other appropriate government authorizations, including the filing of an encryption registration. Governmental regulation of encryption technology and regulation of imports or exports, or our failure to obtain required import or export approval for our products, could harm our international sales and adversely affect our revenue.

Failure to comply with such regulations, whether by us or companies that we have acquired, in the future could result in penalties, costs, and restrictions on export privileges, which could also harm our operating results.

We have, and may further, expand through acquisitions of, or investments in, other companies, which may divert our management’s attention, dilute our stockholders’ ownership interests and consume corporate resources that otherwise would be necessary to sustain and grow our business.

We have made multiple acquisitions in the past, and our business strategy may, from time to time, continue to include acquiring complementary products, technologies or businesses. We also may enter into relationships with other businesses in order to expand our solutions, which could involve preferred or exclusive licenses, additional channels of distribution, or investments by or between the two parties. Negotiating these transactions can be time consuming, difficult and expensive, and our ability to close these transactions may be subject to third‑party approvals, such as government regulation, which are beyond our control. Consequently, we can make no assurance that these transactions, once undertaken and announced, will close.

These transactions may result in unforeseen operating difficulties and expenditures. In particular, we may encounter difficulties assimilating or integrating the businesses, technologies, products, personnel or operations of acquired companies, particularly if the key personnel of the acquired business choose not to work for us, and we may have difficulty retaining the customers of any acquired business. Acquisitions may also disrupt our ongoing business, divert our resources and require significant management attention that would otherwise be available for development of our business. Any acquisition or investment could expose us to unknown liabilities.

In addition, as of March 31, 2021, we had $869.3 million in goodwill and intangible assets, net of accumulated amortization, recorded on our balance sheet. We will incur expenses related to the amortization of intangible assets and we may in the future need to incur charges with respect to the impairment of goodwill or intangible assets, which could adversely affect our operating results. Moreover, we cannot assure you that the anticipated benefits of any acquisition or investment would be realized or that we would not be exposed to unknown liabilities. In connection with these types of transactions, we may issue additional equity securities that would dilute our stockholders’ ownership interests, use cash that we may need in the future to operate our business, incur debt on terms unfavorable to us or that we are unable to repay, incur large charges or substantial liabilities, encounter difficulties integrating diverse business cultures, and become subject to adverse tax consequences, substantial depreciation or deferred compensation charges. These challenges related to acquisitions or investments could adversely affect our business, operating results and financial condition.57

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customers of any acquired business. Acquisitions may also disrupt our ongoing business, divert our resources and require significant management attention that would otherwise be available for development of our business. Any acquisition or investment could expose us to unknown liabilities.

In addition, as of June 30, 2021, we had $854.6 million in goodwill and intangible assets, net of accumulated amortization, recorded on our balance sheet. We will incur expenses related to the amortization of intangible assets and we may in the future need to incur charges with respect to the impairment of goodwill or intangible assets, which could adversely affect our operating results. Moreover, we cannot assure you that the anticipated benefits of any acquisition or investment would be realized or that we would not be exposed to unknown liabilities. In connection with these types of transactions, we may issue additional equity securities that would dilute our stockholders’ ownership interests, use cash that we may need in the future to operate our business, incur debt on terms unfavorable to us or that we are unable to repay, incur large charges or substantial liabilities, encounter difficulties integrating diverse business cultures, and become subject to adverse tax consequences, substantial depreciation or deferred compensation charges. These challenges related to acquisitions or investments could adversely affect our business, operating results and financial condition.

If we are unable to attract and retain qualified employees, lose key personnel, fail to integrate replacement personnel successfully, or fail to manage our employee base effectively, we may be unable to develop new and enhanced solutions, effectively manage or expand our business, or increase our revenue.

Our future success depends upon our ability to recruit and retain key management, technical, sales, marketing, finance, and other critical personnel. Competition for qualified management, technical and other personnel is intense, and we may not be successful in attracting and retaining such personnel. If we fail to attract and retain qualified employees, our ability to grow our business could be harmed. Our officers and other key personnel are employees-at-will, and we cannot assure you that we will be able to retain them. Competition for people with the specific skills that we require is significant. In order to attract and retain personnel in a competitive marketplace, we believe that we must provide a competitive compensation package, including cash and equity‑based compensation. Volatility in our stock price may from time to time adversely affect our ability to recruit or retain employees. If we lose the services of our senior management or other key personnel, including due to illness resulting from COVID-19, if we are unable to hire and retain qualified employees, or conversely, if we fail to manage employee performance or reduce staffing levels when required by market conditions, our business and operating results could be adversely affected.

In addition, hiring, training, and successfully integrating replacement personnel could be time consuming, may cause additional disruptions to our operations, and may be unsuccessful, which could negatively impact future revenue.

Changes in laws and/or regulations related to the Internet or changes in the Internet infrastructure itself may diminish the demand for our solutions, and could have a negative impact on our business.

The future success of our business depends upon the continued use of the Internet as a primary medium for commerce, communication and business applications. Federal, state or foreign government bodies or agencies have in the past adopted, and may in the future adopt, laws or regulations affecting data privacy and the use of the Internet as a commercial medium. Changes in these laws or regulations could require us to modify our solutions in order to comply with these changes. In addition, government agencies or private organizations may begin to impose taxes, fees or other charges for accessing the Internet or commerce conducted via the Internet. These laws or charges could limit the growth of Internet‑related commerce or communications generally, result in a decline in the use of the Internet and the viability of Internet‑based applications such as ours and reduce the demand for our solutions.

The legal and regulatory framework also drives demand for our solutions. Our customers are subject to laws, regulations and internal policies that mandate how they process, handle, store, use and transmit a variety of sensitive data and communications. These laws and regulations are subject to revision, change and interpretation at any time, and any such change could either help or hurt the demand for our solutions. We cannot be sure that the legal and regulatory framework in any given jurisdiction will be favorable to our business or that we will be able to sustain or grow our business if there are any adverse changes to these laws and regulations.

A portion of our revenue is generated by sales to government entities, which are subject to a number of challenges and risks.

Sales to U.S. and foreign federal, state and local governmental agency customers have accounted for a portion of our revenue in past periods, and we may in the future increase sales to government entities. Sales into government entities are subject to a number of risks. Selling to government entities can be highly competitive, expensive and time consuming, often requiring significant upfront time and expense without any assurance that we will win a sale. We have invested in the creation of a cloud offering that has been certified under both the Federal Information Security Management Act and the Federal Risk and Authorization Management Program for government usage but we cannot be sure that we will continue to sustain or renew this certification, that the government will continue to mandate such certification or that other government agencies or entities will use this cloud offering. Government demand and payment for our solutions may be impacted by public sector budgetary cycles and funding authorizations, with funding reductions or delays adversely affecting public sector demand for our solutions. Government entities may have contractual or other legal rights to terminate contracts with our distributors and resellers for convenience or due to a default, and any such termination may adversely impact our future results of operations. For example, if the distributor receives a significant portion of its revenue from sales to such governmental entity, the financial health of the distributor could be substantially harmed, which could negatively affect our future sales to such distributor. Governments routinely investigate and audit government contractors’ administrative processes, and any unfavorable audit could result in the government refusing to continue buying our solutions, a reduction of revenue or fines or civil or criminal liability if the audit uncovers improper or illegal activities. Any such penalties could adversely impact our results of operations in a material way.

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Federal Risk and Authorization Management Program for government usage but we cannot be sure that we will continue to sustain or renew this certification, that the government will continue to mandate such certification or that other government agencies or entities will use this cloud offering. Government demand and payment for our solutions may be impacted by public sector budgetary cycles and funding authorizations, with funding reductions or delays adversely affecting public sector demand for our solutions. Government entities may have contractual or other legal rights to terminate contracts with our distributors and resellers for convenience or due to a default, and any such termination may adversely impact our future results of operations. For example, if the distributor receives a significant portion of its revenue from sales to such governmental entity, the financial health of the distributor could be substantially harmed, which could negatively affect our future sales to such distributor. Governments routinely investigate and audit government contractors’ administrative processes, and any unfavorable audit could result in the government refusing to continue buying our solutions, a reduction of revenue or fines or civil or criminal liability if the audit uncovers improper or illegal activities. Any such penalties could adversely impact our results of operations in a material way.

If we fail to maintain an effective system of internal controls, our ability to produce timely and accurate financial statements or comply with applicable regulations could be impaired.

As a public company, we are subject to the reporting requirements of the Exchange Act, the Sarbanes‑Oxley Act of 2002 (the “Sarbanes-Oxley Act”), and the rules and regulations of the Nasdaq Global Select Market. We expect that the requirements of these rules and regulations will continue to increase our legal, accounting and financial compliance costs, make some activities more difficult, time consuming and costly, and place significant strain on our personnel, systems and resources.

The Sarbanes-Oxley Act requires, among other things, that we maintain effective disclosure controls and procedures and internal control over financial reporting. We are continuing to develop and refine our disclosure controls and other procedures that are designed to ensure that information required to be disclosed by us in the reports that we file with the SEC, is recorded, processed, summarized and reported within the time periods specified in SEC rules and forms, and that information required to be disclosed in reports under the Exchange Act is accumulated and communicated to our principal executive and financial officers.

Our current controls and any new controls that we develop may become inadequate because of changes in conditions in our business. In addition, because we have acquired companies in the past and may continue to do so in the future, we will also need to expend resources to integrate the controls of these acquired entities with ours. Further, weaknesses in our internal controls may be discovered in the future. Any failure to develop or maintain effective controls, or any difficulties encountered in their implementation or improvement, could harm our operating results or cause us to fail to meet our reporting obligations and may result in a restatement of our financial statements for prior periods. Any failure to implement and maintain effective internal controls also could adversely affect the results of periodic management evaluations and annual independent registered public accounting firm report regarding the effectiveness of our internal control over financial reporting that we are required to include in our Annual Report on Form 10-K under Section 404 of the Sarbanes‑Oxley Act. Ineffective disclosure controls and procedures and internal control over financial reporting could also cause investors to lose confidence in our reported financial and other information, which would likely have a negative effect on the trading price of our common stock.

In order to maintain and improve the effectiveness of our disclosure controls and procedures and internal control over financial reporting, we have expended, and anticipate that we will continue to expend, significant resources, including accounting‑related costs, and provide significant management oversight. Any failure to maintain the adequacy of our internal controls, or consequent inability to produce accurate financial statements on a timely basis, could increase our operating costs and could materially impair our ability to operate our business. In the event that we or our independent registered public accounting firm are not able to complete the work required under Section 404 of the Sarbanes-Oxley Act on a timely basis, or we are not able to demonstrate compliance with Section 404, we could be subject to late filings of our annual and quarterly reports, restatements of consolidated financial statements or other corrective disclosure, and, investors may lose confidence in our operating results and our stock price could decline. In addition, if we are unable to continue to meet these requirements, we may not be able to remain listed on the Nasdaq Global Select Market.

We may not be able to utilize a significant portion of our net operating loss or research tax credit carryforwards, which could adversely affect our profitability.

As of ~~March~~June 3130, 2021, we had federal and state net operating loss carryforwards due to prior period losses, some of which if not utilized will continue to expire in 2021 for federal and state purposes. We also have federal research tax credit carryforwards, which will continue to expire in 2021. These net operating loss and research tax credit carryforwards could expire unused and be unavailable to offset future income tax liabilities, which could adversely affect our profitability.

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In addition, under Sections 382 and 383 of the Internal Revenue Code of 1986, as amended, our ability to utilize net operating loss carryforwards or other tax attributes, such as research tax credits, in any taxable year may be limited if we experience an “ownership change.” An “ownership change” generally occurs if one or more stockholders or groups of stockholders who own at least 5% of our stock increase their ownership by more than 50 percentage points over their lowest ownership percentage within a rolling three-year period. Similar rules may apply under state tax laws.

Future issuances of our stock could cause an “ownership change.” It is possible that any future ownership change could have a material effect on the use of our net operating loss carryforwards or other tax attributes, which could adversely affect our profitability.

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Risks Related to Our Convertible Senior Notes

We have indebtedness in the form of convertible senior notes.

In August 2019, we completed an offering of $920.0 million aggregate principal amount of 0.25% Convertible Senior Notes due 2024 (the “2024 Notes”). As a result of this convertible notes offering, we incurred $920.0 million principal amount of indebtedness, the principal amount of which we may be required to pay at maturity in 2024, upon an event of default (as defined in the indenture governing the 2024 Notes (the “indenture”)), or, upon the occurrence of a make-whole fundamental change (as defined in the indenture). There can be no assurance that we will be able to repay this indebtedness when due, or that we will be able to refinance this indebtedness on acceptable terms or at all. In addition, this indebtedness could, among other things:

•

make it difficult for us to pay other obligations;

•

make it difficult to obtain favorable terms for any necessary future financing for working capital, capital expenditures, debt service requirements or other purposes;

•

require us to dedicate a substantial portion of our cash flow from operations to service the indebtedness, reducing the amount of cash flow available for other purposes; and

•

limit our flexibility in planning for and reacting to changes in our business.

Conversion of our 2024 Notes may affect the price of our common stock and the value of the 2024 Notes.

The conversion of some or all of our 2024 Notes may dilute the ownership interest of existing stockholders to the extent we deliver shares of common stock upon conversion. Holders of the 2024 Notes will be able to convert them only upon the satisfaction of certain conditions prior to April 15, 2024. Upon conversion, holders of the 2024 Notes will receive cash, shares of common stock or a combination of cash and shares of common stock, at our election. Any sales in the public market of shares of common stock issued upon conversion of the 2024 Notes could adversely affect the trading price of our common stock and the value of the 2024 Notes.

Our ability to make scheduled payments of the principal of, to pay interest on, or to refinance our indebtedness, including the amounts payable under the 2024 Notes, depends on our future performance, which is subject to economic, financial, competitive, and other factors beyond our control. Our business may not continue to generate cash flow from operations in the future sufficient to service our indebtedness and make necessary capital expenditures. If we are unable to generate such cash flow, we may be required to adopt one or more alternatives, such as selling assets, restructuring debt, or obtaining additional equity capital on terms that may be onerous or highly dilutive. Our ability to refinance our indebtedness will depend on the capital markets and our financial condition at such time. We may not be able to engage in any of these activities or engage in these activities on desirable terms, which could result in a default on our debt obligations.

Further, holders of the 2024 Notes have the right to require us to repurchase all or a portion of their 2024 Notes upon the occurrence of a “fundamental change” (as defined in the indenture) before the maturity date at a repurchase price equal to 100% of the principal amount of the 2024 Notes to be repurchased, plus accrued and unpaid interest, if any. In addition, upon conversion of the 2024 Notes, unless we elect to deliver solely shares of our common stock to settle such conversion (other than paying cash in lieu of delivering any fractional share), we will be required to make cash payments in respect of the 2024 Notes being converted. However, we may not have enough available cash or be able to obtain financing at the time we are required to make repurchases of 2024 Notes surrendered therefor or pay cash with respect of 2024 Notes being converted.

~~The conditional conversion feature of the 2024 Notes, when triggered, may adversely affect our financial condition and operating results.~~60

In the event the conditional conversion feature of the 2024 Notes is triggered, holders of the 2024 Notes will be entitled to convert their 2024 Notes at any time during specified periods at their option. If one or more holders elect to convert their 2024 Notes, unless we elect to satisfy our conversion obligation by delivering solely shares of our common stock (other than paying cash in lieu of delivering any fractional share), we would be required to settle a portion or all of our conversion obligation in cash, which could adversely affect our liquidity. In addition, even if holders of 2024 Notes do not elect to convert their 2024 Notes, we could be required under applicable accounting rules to reclassify all or a portion of the

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~~outstanding~~The ~~principal~~conditional conversion feature of the 2024 Notes, aswhen ~~a current rather than long-term liability~~triggered, ~~which~~may ~~would~~adversely ~~result~~affect inour afinancial ~~material~~condition ~~reduction~~and ofoperating ~~our net working capital~~results.

The capped call transactions may affect the value of the 2024 Notes and our common stock.

In connection with the pricing of the 2024 Notes, we entered into capped call transactions with certain financial institutions. The capped call transactions are expected generally to reduce or offset the potential dilution upon conversion of the 2024 Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted 2024 Notes, as the case may be, with such reduction and/or offset subject to a cap.

In connection with establishing their initial hedges of the capped call transactions, these financial institutions or their respective affiliates likely purchased shares of our common stock and/or entered into various derivative transactions with respect to our common stock concurrently with or shortly after the pricing of the 2024 Notes. These financial institutions or their respective affiliates may modify their hedge positions by entering into or unwinding various derivatives with respect to our common stock and/or purchasing or selling our common stock or other securities of ours in secondary market transactions following the pricing of the 2024 Notes and prior to the maturity of the 2024 Notes (and are likely to do so during any observation period related to a conversion of 2024 Notes). This activity could also cause or avoid an increase or a decrease in the market price of our common stock or the 2024 Notes.

The potential effect, if any, of these transactions and activities on the price of our common stock or the 2024 Notes will depend in part on market conditions and cannot be ascertained at this time. Any of these activities could adversely affect the value of our common stock.

We are subject to counterparty risk with respect to the capped call transactions.

The counterparties to the capped call transactions we entered into in connection with our 2024 Notes are financial institutions, and we will be subject to the risk that one or more of these counterparties may default or otherwise fail to perform, or may exercise certain rights to terminate, their obligations under the capped call agreements. Our exposure to the credit risk of these counterparties will not be secured by any collateral.

If any of these counterparties to one or more of the capped call transactions becomes subject to insolvency proceedings, we will become an unsecured creditor in those proceedings with a claim equal to our exposure at the time under such transaction. Our exposure will depend on many factors but, generally, our exposure will increase if the market price or the volatility of our common stock increases. In addition, upon a default or other failure to perform, or a termination of obligations, by a counterparty, we may suffer less relief from dilution than we currently anticipate with respect to our common stock. We can provide no assurances as to the financial stability or viability of these counterparties.

Risks Related to the Ownership of Our Common Stock

Our stock price has been volatile in the past and may be subject to volatility in the future.

The trading price of our common stock has been volatile historically, and is likely to continue to be subject to wide fluctuations in response to various factors described below. Factors affecting the market price of our securities include:

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the Transaction, the pendency of the Transaction or our failure to complete the Transaction;

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variations in our revenue, billings, gross margin, operating results, free cash flow, loss per share and how these results compare to analyst expectations;

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forward looking guidance that we may provide regarding financial metrics such as billings, revenue, gross margin, operating results, free cash flow, and loss per share;

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announcements of technological innovations, new products or services, strategic alliances, acquisitions or significant agreements by us or by our competitors;

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disruptions in our cloud-based operations or services or disruptions of other prominent cloud-based operations or services;

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