Gessert Erica 4

4 · UPWORK, INC · Filed Mar 20, 2026

AI-generated summary of this filing

Updated Mar 20, 2026

Upwork (UPWK) CFO Erica Gessert Sells 9,278 Shares (Sell-to-Cover)

What Happened

Erica Gessert, Chief Financial Officer of Upwork, had 18,132 restricted stock units (RSUs) convert to common shares on 2026-03-18 (8,433 + 9,699). As part of that conversion/settlement, 9,278 shares were sold in the open market at a weighted average price of $12.31 for total proceeds of $114,231. The conversion/disposition entries showing $0 proceeds reflect shares withheld/used in connection with the RSU settlement and tax withholding.

Key Details

Transaction date: 2026-03-18; Form 4 filed 2026-03-20 (no late filing indicated).
Shares converted (RSU vesting): 8,433 and 9,699 = 18,132 shares (Footnotes F1, F4, F5).
Shares sold: 9,278 shares at a weighted average price of $12.31; proceeds $114,231. Sales executed at prices ranging $12.13–$12.52 (Footnote F3).
Tax withholding / sell-to-cover: The sale represents shares required to be sold to satisfy tax withholding on the RSU vesting (Footnote F2), not a discretionary open-market sale by the insider.
Net shares added from the vesting: 18,132 − 9,278 = 8,854 net shares retained. Total shares owned after the transaction are not specified in the provided excerpt.

Context

These entries reflect RSU vesting and a routine sell-to-cover for taxes rather than a standalone investment decision. For derivative/RSU transactions, it’s common for companies to require or permit withholding/sales to satisfy tax obligations; such transactions are typically administrative and do not necessarily indicate the insider’s market view.

Form 4

Period: 2026-03-18

Chief Financial Officer

Transactions

Exercise/Conversion
Common Stock
[F1]
2026-03-18+8,433→ 306,819 total
Exercise/Conversion
Common Stock
[F1]
2026-03-18+9,699→ 316,518 total
Sale
Common Stock
[F2][F3]
2026-03-18$12.31/sh−9,278$114,231→ 307,240 total
Exercise/Conversion
Restricted Stock Units
[F1][F4]
2026-03-18−8,433→ 67,463 total
→ Common Stock (8,433 underlying)
Exercise/Conversion
Restricted Stock Units
[F1][F5]
2026-03-18−9,699→ 116,397 total
→ Common Stock (9,699 underlying)

Footnotes (5)

[F1]Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
[F2]Represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs listed in Table II. This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a "sell to cover" transaction and does not represent a discretionary trade by the Reporting Person.
[F3]The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $12.13 to $12.52 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon written request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
[F4]The RSUs vest in equal quarterly installments over four years beginning on June 18, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
[F5]The RSUs vest in equal quarterly installments over four years beginning on June 18, 2025, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Signature

/s/ Jacob McQuown, Attorney-in-Fact|2026-03-20

1 file