Upwork (UPWK) CFO Erica Gessert Sells 9,336 Shares (Sell-to-Cover)

What Happened

• Erica Gessert, Chief Financial Officer of Upwork, converted RSU awards (total 18,133 RSUs: 8,433 and 9,700) into common shares on Sept 18, 2026. As required by the company’s sell-to-cover election, she sold 9,336 of those shares in the open market at a weighted average price of $8.45, generating proceeds of $78,897. The conversion entries report $0 proceeds because the RSUs converted to shares (not a cash payment).

Key Details

• Transaction date: 2026-09-18; Form filed: 2026-09-22 (no indication of a late filing).
• Sale: 9,336 shares sold; weighted average price $8.45; per-share sale prices ranged $8.315–$8.52.
• Conversions: 8,433 and 9,700 RSUs converted (total 18,133 shares).
• Net shares from this vesting retained (not sold): 18,133 − 9,336 = 8,797 shares (filing does not state total shares owned after the transaction).
• Footnotes: F1 = each RSU converts to one share; F2 = the sale was a mandatory sell-to-cover to satisfy tax withholding (not a discretionary trade); F3 = reported price is a weighted average; F4/F5 = RSU vesting schedules referenced in the filing.
• Transaction codes: M = exercise/conversion of derivative (RSU conversion here); S = open-market sale; F = tax withholding/sell-to-cover.

Context

• This was primarily a routine sell-to-cover following RSU vesting — a common practice to satisfy tax withholding and not necessarily an indication of the insider’s market view. The RSUs vested/converted and a portion was automatically sold; the filing shows no separate voluntary sale beyond the mandated tax withholding. Purchases would carry more direct bullish signal; this report documents a compensation-related conversion and tax-related sale.