Gessert Erica 4

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.