Anthony Ray Kappus, GM and Chief Operating Officer of Upwork, Inc. (NASDAQ:UPWK), filed a Form 4 on August 20, 2026, disclosing the vesting of restricted stock units and a related tax-withholding share sale that occurred on August 18, 2026.

Key Highlights

  • RSU vesting: 5,115 restricted stock units converted to common shares on August 18, 2026, each representing a right to receive one share of common stock.
  • Shares sold: 1,964 shares were sold at a weighted average price of $8.4257, in multiple transactions ranging from $8.37 to $8.45 per share.
  • Tax-withholding sale: The filing states the sale was mandated by the issuer's "sell to cover" policy and "does not represent a discretionary trade by the Reporting Person."
  • Remaining direct ownership: Kappus directly holds 7,214 shares of common stock following the reported transactions.
  • RSU balance: 71,604 restricted stock units remain beneficially owned directly after the vesting event.
  • Vesting schedule: The RSUs vest in equal quarterly installments over four years beginning May 18, 2026, subject to continued employment.

Upwork COO RSU Vesting, Tax Sale, and Remaining Ownership Details

According to the Form 4 filed with the SEC on August 20, 2026, Anthony Ray Kappus, identified in the filing as GM and Chief Operating Officer of Upwork, Inc., reported two transactions in common stock and one derivative transaction on August 18, 2026. The derivative transaction was the vesting of 5,115 restricted stock units, which the filing describes as a contingent right to receive one share of the issuer's common stock each, at a derivative price of $0.00.

Following that vest, the filing reports a sale of 1,964 shares of common stock. The filing discloses that this sale "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." The reported weighted average sale price was $8.4257 per share, with individual transactions occurring at prices ranging from $8.37 to $8.45 per share. The filing notes that full information on shares sold at each separate price within that range is available upon written request.

After both transactions, Kappus directly holds 7,214 shares of common stock and 71,604 restricted stock units. The filing states the underlying RSU grant vests "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." The form was signed by Jacob McQuown as attorney-in-fact on August 20, 2026.

What Was Disclosed

The filing discloses the August 18, 2026, vesting of 5,115 RSUs and a mandated tax-withholding sale of 1,964 common shares at a weighted average of $8.4257 per share, leaving Kappus with 7,214 shares and 71,604 RSUs directly held.