Gessert Erica 4

What Happened

• Erica Gessert, Chief Financial Officer of Upwork, reported RSU vesting and related transactions on May 18, 2026. A total of 46,024 restricted stock units (37,500 + 8,524) converted into common shares (derivative exercise/conversion). To satisfy tax withholding, 22,162 shares were sold in the open market at a weighted average price of $8.66, generating proceeds of $191,998. Additional shares were withheld/transferred to the issuer to cover tax obligations (no cash proceeds).

Key Details

• Transaction date: May 18, 2026 (Form 4 filed May 20, 2026 — timely).
• Open-market sale: 22,162 shares at a weighted average $8.66 per share (range $8.57–$8.73), proceeds $191,998. (F4)
• Derivative conversions: 37,500 and 8,524 RSUs converted to shares (reported as exercise/conversion, code M). Some converted shares were transferred/withheld for tax obligations at $0.00 (no cash received). (F1, F3)
• Short additional purchase: 1,544 shares acquired under the company’s employee stock purchase plan on May 14, 2026. (F2)
• Vesting notes: RSUs follow the issuer’s vesting schedules described in the filing (some vesting started in 2024 and others begin quarterly from May 18, 2026). (F5, F6)
• Shares owned after the transactions: not specified in the provided filing extract.
• Nature of sale: The sale was a sell-to-cover/tax-withholding action required under Upwork’s equity plans and is not presented as a discretionary market-timing sale by the reporting person. (F3)

Context

• These entries reflect RSU vesting and mandatory tax-withholding mechanics (conversion of RSUs into shares, followed by sell-to-cover and/or shares withheld). Such sell-to-cover transactions are routine and required to satisfy tax liabilities rather than clear indicators of insider sentiment.