Welcome to our dedicated page for UPWORK SEC filings (Ticker: UPWK), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
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.
UPWORK, INC (UPWK) was notified that officer Erica Allen Gessert intends to sell 9,336 shares of its common stock under Rule 144 through Morgan Stanley Smith Barney LLC, with a stated approximate aggregate market value of $78,897.60 as of September 18, 2026 on NASDAQ.
The shares to be sold are described as restricted stock held by the issuer’s officer, and the notice also reports that Gessert sold 22,844 shares of common stock during the prior three months for an aggregate sale price of $192,476.69.
UPWORK, INC (UPWK) is the issuer for a planned resale of common stock under Rule 144 by Hayden Brown through Morgan Stanley Smith Barney. The notice covers 23,893 shares of common stock, with an aggregate market value of $201,917.35, and lists prior sales in the past three months.
Upwork, Inc. (UPWK) officer Anthony Ray Kappus has filed a Form 144 indicating an intent to sell 45,732 shares of Upwork common stock. The planned sale is dated September 18, 2026 and is arranged through Morgan Stanley Smith Barney LLC Executive Financial Services.
The filing reports an aggregate market value of $386,476.56 for the 45,732 shares and references trading on NASDAQ. Over the prior three months, Kappus reported additional sales of 1,964 shares on August 18, 2026 for $16,548.07 and 558 shares on July 20, 2026 for $5,052.97.
UPWORK, INC (UPWK) reported insider transactions by President & CEO Hayden Brown on August 18, 2026. Brown had 46,822 Restricted Stock Units (RSUs) convert into an equal number of common shares, then sold a total of 73,241 shares of common stock. Of these, 23,241 shares were sold to cover tax-withholding obligations mandated by Upwork’s equity plans, while 50,000 shares were sold pursuant to a pre-arranged Rule 10b5-1 plan. The RSUs involved vest in scheduled quarterly installments over four years, contingent on continued employment.
Upwork, Inc. (UPWK) reported that Chief Financial Officer Erica Gessert settled vested equity awards and a related tax sale. On August 18, 2026, RSUs covering 37,500 and 8,524 shares of common stock converted into an equal number of shares. On the same date, 22,844 shares were sold at a $8.4257 weighted average price, in a mandated “sell to cover” transaction to satisfy tax withholding obligations, rather than a discretionary trade. The underlying RSU grants vest over multi-year quarterly schedules, conditioned on continued employment.
UPWORK, INC (UPWK) reported that executive Anthony Ray Kappus, GM & Chief Operating Officer, had 5,115 Restricted Stock Units (RSUs) convert into an equal number of shares of common stock on August 18, 2026. A portion of these shares, 1,964 shares, was sold at a weighted average price of $8.4257 per share to cover tax withholding obligations, as mandated by the company’s equity incentive plan "sell to cover" election and not as a discretionary trade. Following the RSU conversion, 71,604 RSUs remain subject to vesting in equal quarterly installments over four years beginning on May 18, 2026, contingent on Mr. Kappus’s continued employment.
Upwork, Inc. (UPWK) received a notice that its CEO, Hayden Brown, plans to sell shares under Rule 144. A total of 23,241 common shares are indicated for sale through Morgan Stanley Smith Barney LLC, comprising 7,371 performance shares and 15,870 restricted stock, with a filing date of August 18, 2026. Brown previously sold 23,468 common shares over the prior three months for $191,280.63.
Upwork, Inc. (UPWK) is the issuer for a planned sale of common stock by officer Erica Gessert under Rule 144. The notice covers up to 22,844 common shares, with an indicated transaction value of $192,476.69, to be sold through Morgan Stanley Smith Barney LLC, with an earliest sale date of 08/18/2026. In the prior three months, Gessert sold 9,169 common shares on 06/18/2026 for proceeds of $74,733.77.
UPWORK, INC (UPWK) received a notice under Rule 144 that Hayden Brown intends to sell up to 50,000 shares of Upwork common stock through Morgan Stanley Smith Barney LLC. The proposed sale has an indicated aggregate market value of about $409,500.00 based on recent prices and a planned sale date of 08/18/2026.
The shares to be sold were acquired upon the vesting of restricted stock units and performance stock units during the period from 02/18/2024 through 05/18/2024. Upwork reports approximately 124,903,365 shares of common stock outstanding. In the prior three months, Hayden Brown sold 23,468 shares for proceeds of $191,280.63.
Ancient Art, L.P., Trango II, L.L.C. and Quincy J. Lee report significant ownership in Upwork, Inc. common stock. Ancient Art and Trango may be deemed beneficial owners of 7,228,530 shares of common stock held by Teton Capital Partners, L.P., representing 5.8% of Upwork’s outstanding common stock as of June 30, 2026.
Quincy J. Lee may be deemed the beneficial owner of a total of 7,744,477 shares of common stock, or 6.2% of the class, consisting of 7,228,530 shares held by the fund and 515,947 shares held directly. The percentage ownerships are based on 124,797,586 Upwork shares outstanding as of June 30, 2026. Mr. Lee has sole voting and dispositive power over his directly held shares and shared voting and dispositive power, together with the other reporting persons, over the fund’s shares.