Upwork SEC Filings

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.

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.