Upwork SEC Filings

Dave Bottoms, GM, Marketplace at Upwork, Inc. (UPWK), reported issuance and sales tied to restricted stock units (RSUs) and a Rule 10b5-1 plan. On 09/18/2025 and 09/19/2025 the reporting person had multiple non-derivative and derivative transactions: vesting RSUs were recorded (8,980; 6,024; 5,904 RSUs) that convert one-for-one into common shares when vested. To satisfy tax-withholding, 10,894 shares were sold on 09/18/2025 at a weighted average price of $19.1646 and 10,014 shares were sold on 09/19/2025 under a 10b5-1 plan at a weighted average price of $19.9588. Following these transactions the reporting person beneficially owned 345 shares (after the 09/19 sale). The RSUs vest quarterly over four years per the stated grant schedules.

Hayden Brown, President & CEO and Director of Upwork, Inc. (UPWK), reported multiple stock transactions in mid-September 2025. The Form 4 shows Rule 10b5-1 plan sales and vesting of restricted stock units (RSUs). On 09/17/2025 she sold 20,000 shares at $18. On 09/18/2025 she sold 20,000 shares at $19 and sold 22,344 shares at a weighted-average $19.1639 after receiving 17,734 and 28,677 vested RSUs that same day. On 09/19/2025 she sold another 20,000 shares at $20. After these transactions, she beneficially owned 1,082,358 shares. The filer adopted the 10b5-1 plan on December 6, 2024, and some sales were "sell to cover" for tax withholding in connection with RSU vesting.

Upwork, Inc. insider filings show a proposed sale of 10,014 common shares (restricted stock units) acquired on 09/18/2025, with an aggregate market value of $196,274.40, to be sold on 09/19/2025 on NASDAQ. The RSUs were granted by the issuer and paid on the acquisition date. The filer has recorded multiple sales of common stock over the prior three months totaling 29,648 shares with combined gross proceeds of $425,480.53 (sales on 08/08/2025, 08/18/2025, 08/29/2025, and 09/18/2025). The notice includes the standard insider representation that no material non-public information is known.

Insider sale notice for UPWK common stock. The filing reports a proposed sale of 20,000 shares through Morgan Stanley Smith Barney with an aggregate market value of $392,000, with an approximate sale date of 09/19/2025 on NASDAQ. The shares were acquired as Restricted and Performance Stock Units on 06/18/2020. The filing also discloses multiple recent sales by or for Hayden L. Brown during Aug–Sep 2025 totaling 147,921 shares and generating gross proceeds of $2,347,515.56 across listed transactions. The filer certifies no undisclosed material adverse information and references reliance on Rule 10b5-1 trading instructions where applicable.

Form 144 notice for Upwork, Inc. (UPWK) reports a proposed sale of 8,730 common shares through Morgan Stanley Smith Barney on NASDAQ with an aggregate market value of $167,302.59. The filer indicates those shares were acquired as restricted stock from the issuer and the acquisition and proposed sale are both dated 09/18/2025. The filing also discloses a prior sale by the same person, Erica Gessert, of 19,036 shares on 08/18/2025 for gross proceeds of $263,364.96. The document contains the broker name and the total shares outstanding reported as 132,606,579. The standard signature representation affirms no undisclosed material adverse information.

Upwork, Inc. Form 144 filing: This notice reports a proposed sale of 22,344 shares of Upwork common stock by an affiliated person, to be executed through Morgan Stanley Smith Barney LLC on 09/18/2025 with an aggregate market value of $428,202.65 based on the filing. The securities are described as restricted stock acquired from the issuer on 09/18/2025 and the filing indicates prior sales by the same person, Hayden Brown, totaling 103,577 shares across three transactions in the past three months, generating gross proceeds of $1,539,310.36. The filer certifies no undisclosed material adverse information.

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. 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.