UPWORK, INC·4

Mar 20, 4:49 PM ET

Bottoms Dave 4

4 · UPWORK, INC · Filed Mar 20, 2026

Research Summary

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Upwork (UPWK) GM Dave Bottoms Exercises RSUs, Sells Shares

What Happened

  • Dave Bottoms, GM, Marketplace at Upwork, converted a total of 20,908 vested RSUs into common stock on March 18, 2026. The converted shares were reported as "exercise/conversion" and an equal number (20,908) were reported as disposed at $0.00 to satisfy tax withholding (sell‑to‑cover).
  • Separately, Bottoms sold 11,575 shares on March 18 at a weighted average price of $12.31 for approximately $142,509, and sold 7,000 shares on March 19 at a weighted average price of $11.49 for approximately $80,448. Total reported cash proceeds from the open‑market sales = $222,957.

Key Details

  • Transaction dates: RSU conversions and sell‑to‑cover on 2026-03-18; open‑market sales on 2026-03-18 and 2026-03-19. Filing date: 2026-03-20 (timely).
  • RSUs converted: 8,980 + 6,024 + 5,904 = 20,908 shares; same 20,908 reported as withheld/surrendered for tax (reported as derivative dispositions at $0).
  • Open‑market sales: 11,575 shares @ weighted $12.31 (range $12.13–$12.52) = $142,509; 7,000 shares @ weighted $11.49 (range $11.33–$11.72) = $80,448. One open‑market sale was effected pursuant to a Rule 10b5‑1 trading plan adopted May 30, 2025.
  • Footnotes: F2 = sell‑to‑cover mandated under issuer’s equity plan (not a discretionary trade). F3/F5 = reported prices are weighted averages with ranges; full price breakdowns available on request.
  • Shares owned after transaction: Not reported in this Form 4.

Context

  • These were RSU conversions (not option purchases) with immediate withholding/sale to cover taxes — a common administrative step that does not necessarily indicate an additional voluntary sale decision for the withheld portion.
  • The additional open‑market sales generated cash proceeds and included at least one 10b5‑1 plan trade, which is an automated trading plan established earlier (May 30, 2025). Such sales can be pre‑scheduled and are not necessarily contemporaneous expressions of sentiment.

Insider Transaction Report

Form 4
Period: 2026-03-18
Bottoms Dave
GM, Marketplace
Transactions
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-03-18+8,9809,325 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-03-18+6,02415,349 total
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-03-18+5,90421,253 total
  • Sale

    Common Stock

    [F2][F3]
    2026-03-18$12.31/sh11,575$142,5099,678 total
  • Sale

    Common Stock

    [F4][F5]
    2026-03-19$11.49/sh7,000$80,4482,678 total
  • Exercise/Conversion

    Restricted Stock Units

    [F1][F6]
    2026-03-188,98017,960 total
    Common Stock (8,980 underlying)
  • Exercise/Conversion

    Restricted Stock Units

    [F1][F7]
    2026-03-186,02448,188 total
    Common Stock (6,024 underlying)
  • Exercise/Conversion

    Restricted Stock Units

    [F1][F8]
    2026-03-185,90470,850 total
    Common Stock (5,904 underlying)
Footnotes (8)
  • [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]This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025.
  • [F5]The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $11.33 to $11.72 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.
  • [F6]The RSUs vest in equal quarterly installments over four years beginning on December 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
  • [F7]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.
  • [F8]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

Documents

2 files