Gessert Erica 4
4 · UPWORK, INC · Filed Feb 19, 2026
Research Summary
AI-generated summary of this filing
Upwork (UPWK) CFO Erica Gessert Receives Award, Sells Shares
What Happened
Erica Gessert, Chief Financial Officer of Upwork (UPWK), had equity awards convert/vest and sold a portion to cover tax withholding. The filing shows conversion/exercise of 40,477 shares on 2026-02-17 and 37,500 shares on 2026-02-18 (derivative conversions), plus a grant/award/acquisition of 136,388 shares on 2026-02-18. She sold 26,292 shares in an open-market transaction at a weighted-average price of $13.80, generating $362,887 in proceeds. The conversion lines report $0 proceeds because they reflect vesting/conversion of RSUs/PSUs (non-cash settlement).
Key Details
- Transaction dates: conversions on 2026-02-17 and 2026-02-18; open-market sale on 2026-02-18. Filing date: 2026-02-19 (timely).
- Sale price/amount: 26,292 shares sold at a weighted average of $13.80 (range $13.34–$14.085), proceeds $362,887.
- Awards/vesting: 136,388 RSU/PSU shares reported acquired (derivative award). Footnote indicates PSUs for the performance period ending 12/31/2025 vested 100% upon certification on 2/17/2026.
- Tax withholding: The sale of 26,292 shares was a mandated "sell-to-cover" to satisfy tax withholding; not a discretionary sell by the insider (footnote).
- Shares owned after transaction: not specified in the provided filing excerpt.
- No 10b5-1 plan or late filing noted in this report.
Context
- These were largely non-cash equity vesting/conversions (RSUs/PSUs converting into shares). The subsequent open-market sale was a routine sell-to-cover to meet tax obligations, which is common after vesting and doesn’t necessarily indicate a change in sentiment.
- For retail investors: purchases are usually stronger signals than routine vesting or sell-to-cover transactions. This filing primarily documents compensation-related vesting and the required tax withholding sale.
Insider Transaction Report
Form 4
UPWORK, INCUPWK
Gessert Erica
Chief Financial Officer
Transactions
- Exercise/Conversion
Common Stock
[F1]2026-02-17+40,477→ 287,178 total - Exercise/Conversion
Common Stock
[F1]2026-02-18+37,500→ 324,678 total - Sale
Common Stock
[F2][F3]2026-02-18$13.80/sh−26,292$362,887→ 298,386 total - Exercise/Conversion
Performance Stock Units
[F1][F4]2026-02-17−40,477→ 0 total→ Common Stock (40,477 underlying) - Exercise/Conversion
Restricted Stock Units
[F1][F5]2026-02-18−37,500→ 187,500 total→ Common Stock (37,500 underlying) - Award
Restricted Stock Units
[F1][F6]2026-02-18+136,388→ 136,388 total→ Common Stock (136,388 underlying)
Footnotes (6)
- [F1]Each restricted stock unit ("RSU") or performance stock unit ("PSU") 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 or PSUs 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 $13.34 to $14.085 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]Represents earned PSUs that vested based on the achievement of performance criteria for a performance period that ended on December 31, 2025, as certified by the compensation committee of the board of directors of the Issuer on February 17, 2026. The earned PSUs vested 100% upon certification.
- [F5]The RSUs vest 25% on May 18, 2024 and then 1/16th of the total number of shares on each quarterly anniversary thereafter, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
- [F6]The RSUs vest in equal quarterly installments over four years beginning on May 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
Signature
/s/ Jacob McQuown, Attorney-in-Fact|2026-02-19