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. GM, Marketplace Dave Bottoms reported a mix of RSU vesting and share sales. On March 18, 2026, he converted a total of 20,908 Restricted Stock Units into an equal number of common shares at a conversion price of $0.00 per share, reflecting routine equity compensation vesting.
On the same day, he sold 11,575 common shares at a weighted average price of $12.3118 per share, followed by an additional sale of 7,000 shares on March 19, 2026 at a weighted average price of $11.4926 per share. Footnotes state that part of the shares sold were required to cover tax withholding obligations through a “sell to cover” transaction under Upwork’s equity incentive plans, meaning those sales were not discretionary trades.
Another footnote explains that the transactions were effected pursuant to a Rule 10b5-1 trading plan adopted on May 30, 2025, indicating the sales were pre-planned. After these transactions, Bottoms directly holds 2,678 shares of Upwork common stock, alongside ongoing RSU awards that vest in equal quarterly installments over four-year periods beginning on December 18, 2022, June 18, 2024, and June 18, 2025, subject to continued employment.
Upwork affiliate filed a notice to sell 7,000 Restricted Stock Units on 03/18/2026. The filing lists Morgan Stanley Smith Barney LLC as the broker-dealer for the proposed sale. The excerpt also discloses recent Rule 10b5-1 sales by David Bottoms: 03/18/2026 (11,575 shares), 02/19/2026 (15,649 shares) and 02/18/2026 (17,013 shares) with reported gross proceeds for each trade.
Upwork filed a Form 144 proposing the sale of 11,575 restricted shares to be sold on 03/18/2026.
Prior reported dispositions by David T. Bottoms include 15,649 shares on 02/19/2026 for $211,441.46, 17,013 shares on 02/18/2026 for $236,423.49, and 9,622 shares on 12/19/2025 for $198,807.84.
Erica Gessert filed a Form 144 reporting a proposed sale of 9,278 restricted shares of common stock of UPWK to be effected on 03/18/2026. The filing lists the securities as Restricted Stock and names Morgan Stanley Smith Barney LLC as the broker. It also discloses 26,292 shares of common stock sold on 02/18/2026 in the past three months.
Upwork Inc. reporting a Form 144 notice: Hayden Brown proposes to sell 23,745 shares of restricted common stock on 03/18/2026.
The filing also discloses prior sales on 02/18/2026 of 73,152 shares for $1,014,011.69 and 50,000 shares for $689,300.00. The notice lists security type as Restricted Stock and the exchange as NASDAQ.
Upwork Inc. reported that GM, Marketplace David T. Bottoms has agreed to resign, remaining with the company through April 3, 2026. A separation agreement signed on March 17, 2026 provides him, subject to a release of claims, a lump-sum payment equal to twelve months of base salary and reimbursement of COBRA health insurance premiums for up to twelve months or until he gains comparable coverage elsewhere or becomes ineligible.
His outstanding equity awards will continue to vest through his last day of employment. Effective April 4, 2026, GM & Chief Operating Officer Anthony Kappus will lead all marketplace-related teams except engineering, which will be led by Chief Technology Officer & Head of AI/ML Andrew Rabinovich, consolidating marketplace and technology leadership after Bottoms’s departure.
Upwork, Inc.’s Chief Financial Officer Erica Gessert reported multiple equity-related transactions. On February 17–18, 2026, performance stock units and restricted stock units converted into common stock, and she also received a new grant of 136,388 RSUs that vest quarterly over four years beginning May 18, 2026.
To satisfy tax withholding obligations from these vestings, 26,292 shares of common stock were automatically sold in a mandated “sell to cover” transaction at a weighted average price of $13.8022 per share, within a range of $13.34 to $14.085. After these transactions, she directly held 298,386 shares of common stock and 187,500 RSUs.
Upwork, Inc. GM, Marketplace Dave Bottoms reported a mix of stock sales, vesting, and equity awards. He sold a total of 32,662 shares of common stock in open-market transactions at weighted average prices of $13.5115 and $13.802 per share, leaving 345 common shares directly held afterward.
Footnotes state that part of the shares sold were required to cover tax withholding obligations from vesting RSUs or PSUs under a mandated “sell to cover” arrangement, so those sales were not discretionary. At least one sale was executed under a Rule 10b5‑1 trading plan adopted on May 30, 2025.
On the acquisition side, Bottoms had 28,912 performance stock units vest after performance for a period ending December 31, 2025 was certified, and 3,750 RSUs were converted into common stock. He also received a grant of 81,833 RSUs that vest quarterly over four years beginning May 18, 2026.
Upwork, Inc. President & CEO Hayden Brown reported multiple equity transactions involving RSUs, PSUs and common stock. On February 17–18, 2026, Brown exercised and converted several batches of restricted and performance stock units into common shares at a price of $0.00 per share, and received a new grant of 218,221 restricted stock units, each representing a contingent right to one share of common stock.
Following these equity awards and conversions, Brown conducted open‑market sales totaling 123,152 shares of common stock at weighted average prices around the mid‑$13 range per share. According to the footnotes, a portion of these shares was sold to cover tax withholding obligations mandated under Upwork’s equity incentive plans, and the transactions were carried out under a pre‑arranged Rule 10b5‑1 trading plan. After these transactions, Brown directly owned 776,067 shares of common stock and 218,221 RSUs.
David Bottoms reported insider sales of UPWK common stock under Rule 144. The filing lists sales of 17,013 shares on 02/18/2026 for $236,423.49, 9,622 shares on 12/19/2025 for $198,807.84 (noted as a 10b5-1 plan), and 11,285 shares on 12/18/2025 for $232,334.45. The filing also lists 13,879 Performance Stock Units and 1,770 Restricted Stock Units dated 02/18/2026.