Upwork Inc. filings document regulatory disclosures for an operating company whose marketplace connects businesses with AI-enabled talent and contingent work services. Form 8-K reports furnish quarterly and annual financial results, conference-call materials, GAAP and non-GAAP reconciliations, and Regulation FD disclosures tied to business and financial performance.
The filing record also covers governance and capital-structure matters, including definitive proxy disclosures on executive compensation, equity awards and pay-versus-performance data; officer appointments and departures under Item 5.02; and board-authorized common-stock repurchase programs disclosed in material-event reports.
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 2,035 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.
Marie Olivier, Chief Accounting Officer of Upwork, Inc. (UPWK), reported several transactions in August 2025. On 08/14/2025 she sold 1,294 shares under a Rule 10b5-1 plan at a weighted average price of $14 per share. On 08/18/2025 she had restricted stock units vest and be settled: 1,427 RSUs and 1,200 RSUs (each RSU converts to one share). To satisfy tax withholding upon vesting, she had 941 shares sold in a sell-to-cover at a weighted average price of $13.8367 per share. Following the reported transactions, she beneficially owned 2,434 shares (after the 08/14 sale) and later 3,375 and 2,434 shares as shown in the filing; Table II shows 2,854 and 2,400 underlying shares resulting from the settled RSUs. The filing states the 08/14 sale was pursuant to a 10b5-1 plan adopted May 15, 2025, and that sell-to-cover was required by the issuer's equity plan.
Form 144 filed for Upwork Inc. (UPWK) reporting planned sale of common stock by an insider through Morgan Stanley Smith Barney. The notice lists 25,577 shares offered for sale with an aggregate market value of $353,860.35 and an approximate sale date of 08/18/2025 on NASDAQ. The filing shows the shares were acquired on 08/18/2025 as performance shares (12,407) and restricted stock (13,170), with acquisition payment noted as not applicable. Recent selling activity by the same person, HAYDEN BROWN, is disclosed: sales on 06/18/2025 (23,716 shares, $320,291.69), 05/19/2025 (12,824 shares, $214,349.31) and 05/19/2025 (13,614 shares, $227,553.93). The filer certifies no undisclosed material adverse information and includes the standard attestation language for Rule 144 notices.
Form 144 filed for UPWK: insider sale notice and recent insider transactions. The filing shows a proposed sale of 2,060 common shares through Morgan Stanley Smith Barney with an aggregate market value of $28,500.31 and an approximate sale date of 08/18/2025. The shares are listed as restricted stock acquired on 08/18/2025. The filer, identified in prior sales as David Bottoms, sold 24,312 common shares across four transactions in the past three months, generating gross proceeds totaling $333,270.18. The issuer's number of shares outstanding is reported as 132,606,579, making the planned sale a very small fraction of outstanding shares. The filer certifies no undisclosed material adverse information.
Upwork Inc. (UPWK) Form 144 notice: The filing discloses a proposed sale of 19,036 restricted common shares, with an aggregate market value of $263,364.96, against a reported 132,606,579 shares outstanding. The proposed approximate sale date is 08/18/2025 on NASDAQ. The shares were acquired as restricted stock on 08/18/2025 from the issuer and reported as paid in full on that date. The filer also reported two prior sales by the same person in the last three months: 9,267 shares on 06/18/2025 for $125,153.62 and 19,677 shares on 05/19/2025 for $328,895.15. The notice includes the required representation that the seller is unaware of undisclosed material adverse information.
Form 144 notice for Upwork Inc. (UPWK): An insider, Hayden L Brown, reported intent to sell 60,000 common shares through Morgan Stanley Smith Barney LLC on 08/15/2025 on the NASDAQ exchange. The filing lists an aggregate market value of $822,000 for the shares and shows 132,606,579 shares outstanding. The securities were acquired as RSU/PSU from the issuer on 06/18/2019. The filing also discloses two sales by the same person in the past three months: 23,716 shares sold on 06/18/2025 for $320,294.07 and 26,438 shares sold on 05/19/2025 for $438,382.63. No relationship to the issuer is specified in the provided text.
Upwork Inc. announced the appointment of Anthony Kappus as Chief Operating Officer, effective September 2, 2025. Mr. Kappus joins after 11 years at Redfin, where he served in roles including Chief of Digital Revenue and Chief Legal Officer.
His initial compensation includes an annual base salary of $500,000, a target annual bonus equal to 60% of base salary, and a restricted stock unit award equal to $7,250,000 divided by the 30-day average closing price prior to grant. The RSU vests 25% on September 18, 2026 and 6.25% on each quarterly anniversary thereafter. The Severance Agreement provides 12 months base salary and up to 12 months of continued medical premiums if terminated without cause, and in specified change-in-control windows adds a pro-rated bonus and 100% acceleration of then-unvested equity and cash awards (excluding performance-vested awards). The company disclosed no related-party arrangements and furnished a press release as Exhibit 99.1.