Upwork, Inc. Chief Financial Officer Erica Gessert filed a Form 4 on August 20, 2026, disclosing the vesting of restricted stock units and a mandatory tax-withholding sale of common stock that occurred on August 18, 2026.

Key Highlights

  • RSU vesting - first grant: 37,500 restricted stock units converted to common stock on August 18, 2026, via transaction code M.
  • RSU vesting - second grant: 8,524 restricted stock units converted to common stock on August 18, 2026, via transaction code M.
  • Mandatory sell-to-cover: 22,844 shares were sold at a weighted average price of $8.4257, with individual transactions ranging from $8.37 to $8.45 per share.
  • Post-transaction ownership: Gessert directly held 364,789 shares of common stock following the reported transactions.
  • Remaining RSUs: 112,500 and 119,340 derivative securities (RSUs) remained beneficially owned directly after the transactions.
  • Sale characterization: According to the filing, the sale was "mandated by the Issuer's election" and "does not represent a discretionary trade by the Reporting Person."

Upwork CFO RSU Vesting Details and Tax-Withholding Sale on August 18, 2026

According to the filing, Erica Gessert, Chief Financial Officer of Upwork, Inc. (NASDAQ:UPWK), reported two separate RSU vesting events on August 18, 2026. The first involved 37,500 restricted stock units converting to an equal number of shares of common stock. The second involved 8,524 restricted stock units similarly converting to common shares. The filing notes that each RSU represents "a contingent right to receive one share of the Issuer's common stock."

Following the two vesting events, the filing discloses that 22,844 shares were sold at a weighted average price of $8.4257 per share, with individual transactions executed at prices ranging from $8.37 to $8.45 per share. The filing states this sale was required to cover tax withholding obligations arising from the RSU vestings and was mandated by the issuer's equity incentive plan through a "sell to cover" arrangement, not a discretionary decision by Gessert. After all reported transactions, Gessert directly held 364,789 shares of common stock.

The filing also details the vesting schedules for the two RSU grants. The first grant vests 25% on May 18, 2024, and then 1/16th of the total shares on each quarterly anniversary thereafter, subject to continued employment. The second grant vests in equal quarterly installments over four years beginning on May 18, 2026, also subject to continued employment. Following the transactions, Gessert retained 112,500 RSUs from the first grant and 119,340 RSUs from the second grant, both held directly. The form was signed by Jacob McQuown as Attorney-in-Fact on August 20, 2026.

What Was Disclosed

The filing reports two RSU vesting transactions totaling 46,024 shares for Upwork's CFO on August 18, 2026, followed by a company-mandated sale of 22,844 shares to satisfy tax withholding obligations, leaving Gessert with 364,789 shares held directly.