Upwork SEC Filings

Upwork, Inc. insider notice reports a proposed sale of 10,894 restricted common shares through Morgan Stanley Smith Barney on 09/18/2025 with an aggregate market value of $208,773.71 based on the filing. The filing shows the shares were acquired as restricted stock from the issuer on 09/18/2025. The filer also reported three recent open-market sales by the same person in August 2025 totaling 12,750 shares for gross proceeds of $162,701.01. The issuer has 132,606,579 shares outstanding per the notice.

Upwork, Inc. (UPWK) insider Hayden L. Brown filed a Form 144 to sell 20,000 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $362,800.00, scheduled approximately for 09/18/2025. The filing shows these shares were originally acquired as PSU/RSU on 06/18/2020. The issuer's outstanding shares are listed as 132,606,579. The notice also discloses three recent sales during the past three months attributed to the same account, including 20,000 shares on 09/17/2025 for $360,000.00, 25,577 shares on 08/18/2025 for $353,862.91, and 60,000 shares on 08/15/2025 for $825,450.00. The filing includes the standard representation regarding absence of undisclosed material information and references reliance on Rule 10b5-1 where applicable.

Upwork, Inc. (UPWK) insider Hayden L. Brown filed a Form 144 to sell 20,000 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $362,800.00, scheduled approximately for 09/18/2025. The filing shows these shares were originally acquired as PSU/RSU on 06/18/2020. The issuer's outstanding shares are listed as 132,606,579. The notice also discloses three recent sales during the past three months attributed to the same account, including 20,000 shares on 09/17/2025 for $360,000.00, 25,577 shares on 08/18/2025 for $353,862.91, and 60,000 shares on 08/15/2025 for $825,450.00. The filing includes the standard representation regarding absence of undisclosed material information and references reliance on Rule 10b5-1 where applicable.

Upwork, Inc. (UPWK) insider Hayden L. Brown filed a Form 144 to sell 20,000 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $362,800.00, scheduled approximately for 09/18/2025. The filing shows these shares were originally acquired as PSU/RSU on 06/18/2020. The issuer's outstanding shares are listed as 132,606,579. The notice also discloses three recent sales during the past three months attributed to the same account, including 20,000 shares on 09/17/2025 for $360,000.00, 25,577 shares on 08/18/2025 for $353,862.91, and 60,000 shares on 08/15/2025 for $825,450.00. The filing includes the standard representation regarding absence of undisclosed material information and references reliance on Rule 10b5-1 where applicable.

Upwork, Inc. insider sale notice: This Form 144 shows an intended sale of 20,000 common shares by a person for whose account the securities are to be sold, through Morgan Stanley Smith Barney on 09/17/2025, with an aggregate market value of $342,000.00. The shares were originally acquired as Restricted and Performance Stock Units on 11/18/2022. The filing also discloses three recent sales by the same person totaling 109,293 shares with gross proceeds of $1,499,606.98, including an explicit Rule 10b5-1 plan sale of 60,000 shares on 08/15/2025. Outstanding shares noted are 132,606,579.

Upwork, Inc. insider sale notice: This Form 144 shows an intended sale of 20,000 common shares by a person for whose account the securities are to be sold, through Morgan Stanley Smith Barney on 09/17/2025, with an aggregate market value of $342,000.00. The shares were originally acquired as Restricted and Performance Stock Units on 11/18/2022. The filing also discloses three recent sales by the same person totaling 109,293 shares with gross proceeds of $1,499,606.98, including an explicit Rule 10b5-1 plan sale of 60,000 shares on 08/15/2025. Outstanding shares noted are 132,606,579.

Dave Bottoms, listed as an officer (GM, Marketplace) of Upwork, Inc. (UPWK), reported a sale of 1,690 shares of Upwork common stock on 08/29/2025 at a price of $14.95 per share. The filing shows 345 shares remained beneficially owned by the reporting person after the transaction. The sale was executed under a Rule 10b5-1 trading plan adopted by the reporting person on May 30, 2025, and the Form 4 was signed by an attorney-in-fact, Jacob McQuown, on 09/03/2025. No derivatives or additional transactions are reported in this filing.

Upwork Inc. furnished a press release reporting a 2025 Share Repurchase Authorization, with the release attached as Exhibit 99.1 to this Form 8-K. The filing states the information in Item 7.01 and Exhibit 99.1 is being furnished (not "filed") for purposes of the Exchange Act, limiting incorporation and Section 18 liabilities. A date of September 3, 2025 appears in the filing.

Form 144 notice from an insider at Upwork Inc. (UPWK) discloses a proposed sale of 1,690 common shares through Morgan Stanley Smith Barney on 08/29/2025 with an aggregate market value of $25,197.90. The securities were acquired as Restricted Stock Units on 08/18/2025 and payment was marked N/A. The filing also lists three recent sales by the same person, David Bottoms: 2,060 shares on 08/18/2025 (gross $28,504.22), 9,000 shares on 08/08/2025 (gross $115,937.10), and 11,562 shares on 06/18/2025 (gross $156,149.43). The notice includes the required attestation that the seller lacks undisclosed material adverse information.

Marie Olivier, Chief Accounting Officer at Upwork, Inc. (UPWK), reported the sale of 1,686 shares of common stock on 08/19/2025 under a Rule 10b5-1 trading plan adopted May 15, 2025. The shares were sold in multiple transactions at prices ranging from $13.86 to $13.91, producing a reported weighted-average price of $13.8821 per share. The filing was signed by an attorney-in-fact on 08/21/2025. The reporting person discloses she beneficially owned 748 shares after the disposals. The filer offers to provide detailed per-trade quantities and prices upon written request.

Erica Gessert, Chief Financial Officer of Upwork, Inc. (UPWK) reported equity activity related to restricted stock units and a sell-to-cover tax-withholding transaction. On 08/18/2025, 37,500 RSUs vested, converting to 37,500 shares of common stock that were recorded as acquired. To satisfy tax withholding required by the company's equity plan, 19,036 shares were sold in multiple transactions at a weighted average price of $13.8352 per share (prices ranged $13.74–$13.987). After these transactions the reporting person held 209,202 shares of common stock and beneficially owned 262,500 shares underlying RSUs.

The filing notes the sell-to-cover was mandated by the issuer's election under its equity incentive plans and does not reflect a discretionary sale by the reporting person.

Dave Bottoms, an officer (GM, Marketplace) of Upwork, Inc. (UPWK), reported equity activity on 08/18/2025. 3,750 restricted stock units (RSUs) vested and were recorded as acquired, representing the contingent right to receive one share each. Concurrently, 2,060 shares were sold to satisfy tax-withholding obligations under the company’s mandatory "sell-to-cover" program at a weighted-average price of $13.837 per share (sales ranged $13.74–$13.987). After these transactions, the filing shows the reporting person directly beneficially owned 4,095 shares of common stock and held 22,500 RSUs total. The sale to cover was not a discretionary trade but a plan-mandated withholding method.

Upwork Inc. director and President & CEO Hayden Brown reported multiple transactions in August 2025 that changed her beneficial ownership of Upwork (UPWK) common stock. On August 15, 2025 she sold 60,000 shares under a Rule 10b5-1 plan at a weighted-average price of $13.7575, leaving her with 1,093,485 shares. Between August 18, 2025 transfers and vesting converted RSUs into shares, adding a total of 50,383 shares, and a "sell to cover" sale of 25,577 shares occurred to satisfy tax withholding at a weighted-average price of $13.8352. After these events her reported beneficial ownership is 1,118,291 shares. Several RSU awards remain subject to future vesting schedules.