Every Form 4 that Upwork Inc. (UPWK) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow UPWK and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full UPWK filings page.
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.’s GM & Chief Operating Officer Anthony Ray Kappus reported RSU vesting on July 18, 2026, converting 1,412 RSUs into the same number of common shares at no cost. To satisfy tax withholding from this vesting, 558 shares were automatically sold in a required “sell to cover” transaction at a weighted average price of $9.0554 per share. After the transaction, he reported holding 21,191 RSUs that vest in equal quarterly installments over four years beginning July 18, 2026, subject to continued employment.
UPWORK, INC Chief Financial Officer Erica Gessert reported routine equity compensation activity involving RSUs and a related tax sale. On June 18 2026, 18,132 restricted stock units converted into the same number of common shares. To cover tax withholding on this vesting, 9,169 common shares were sold in a mandated “sell to cover” transaction at a weighted average price of $8.1507 per share, with actual sale prices ranging from $8.02 to $8.25 per share. The filing notes this sale did not represent a discretionary trade by Gessert. Following these transactions, she directly holds 341,609 shares of Upwork common stock. The RSU awards continue to vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to her continued employment.
Upwork, Inc. Chief Accounting Officer Sabrina Mekhalfa reported routine equity transactions tied to restricted stock units (RSUs). She exercised RSUs covering 3,577 units, receiving the same number of common shares at a $0.00 exercise price. On the same date, 1,276 common shares were sold at a weighted average price of $8.1509 per share to cover tax withholding obligations under the company’s equity incentive plans, described as a mandatory “sell to cover” transaction rather than a discretionary trade. Following these transactions, she directly holds 4,396 shares of Upwork common stock.
Upwork, Inc. President & CEO Hayden Brown reported routine equity compensation activity involving restricted stock units (RSUs) and a related tax sale. On June 18, 2026, Brown sold 23,468 shares of common stock at a weighted average price of $8.1507 per share to cover tax withholding obligations tied to RSU vesting, as required by the company’s “sell to cover” election and not as a discretionary trade.
On the same date, Brown also acquired 46,411 shares of common stock through the vesting and settlement of RSUs. Following these transactions, she directly holds 797,495 shares of Upwork common stock and continues to hold additional unvested RSUs subject to quarterly vesting over four-year schedules.
BRAMLEY CLAIRE reported acquisition or exercise transactions in this Form 4 filing.
Upwork, Inc. director Claire Bramley received an equity award in the form of 45,146 restricted stock units (RSUs) of common stock. The RSUs vest in three equal installments: one-third on June 4, 2027, one-third on June 4, 2028, and the final third on the earlier of the date immediately prior to Upwork’s 2029 annual stockholders’ meeting or December 31, 2029, in each case conditioned on continued service.
LISSY DAVID H reported acquisition or exercise transactions in this Form 4 filing.
Upwork director David H. Lissy reported receiving two new grants of Upwork common stock in the form of restricted stock units (RSUs). One award covers 20,880 shares that vest in three equal parts on June 4, 2027, June 4, 2028, and the earlier of the date immediately prior to Upwork’s 2029 annual stockholder meeting or December 31, 2029, subject to continued service. A second award covers 45,146 RSUs that vest 100% on the earlier of the date immediately prior to the 2027 annual meeting or June 4, 2027, also conditioned on continued service.
LAYTON THOMAS reported acquisition or exercise transactions in this Form 4 filing.
Upwork, Inc. director Thomas Layton reported new equity awards in the form of Restricted Stock Units (RSUs) rather than any open-market trading. On June 4, 2026, he received three RSU grants covering 20,880, 6,772, and 6,207 shares of common stock at no cash cost.
One RSU award vests quarterly over four quarters starting on September 30, 2026, with the final installment fully vesting by the earlier of the 2027 annual meeting or June 30, 2027, subject to continued service. Another RSU grant vests 100% by the earlier of the 2027 annual meeting or June 4, 2027, also conditioned on continued service.
The filing notes that a trust for Layton’s benefit now holds 1,639,134 shares of Upwork common stock indirectly, and separately references a gift of 21,365 shares to that trust. These entries describe compensation and estate-planning movements, not buys or sells in the market.
KELMAN GLENN reported acquisition or exercise transactions in this Form 4 filing.
Upwork director Glenn Kelman received two equity awards in the form of restricted stock units (RSUs). One grant covers 20,880 RSUs that vest quarterly over four quarters starting on September 30, 2026, with the final installment vesting no later than June 30, 2027, subject to continued service. A second grant covers 6,207 RSUs that vest 100% on the earlier of the date immediately prior to Upwork’s 2027 annual meeting of stockholders or June 4, 2027, also contingent on continued service.
Upwork, Inc. director Gary Steele reported two equity awards of common stock. On June 4, 2026, he acquired 20,880 RSUs and 6,207 RSUs as compensation at no purchase price. These are restricted stock units that convert into shares as they vest over time.
The 20,880 RSUs vest quarterly over four quarters, starting on September 30, 2026, with the final quarterly portion fully vesting on the earlier of the day before Upwork’s 2027 annual stockholder meeting or June 30, 2027, subject to his continued service. The 6,207 RSUs vest 100% on the earlier of the day before the 2027 annual meeting or June 4, 2027, also contingent on continued service. These are routine director compensation grants, not open‑market share purchases or sales.
EVAN DANA L reported acquisition or exercise transactions in this Form 4 filing.
Upwork, Inc. director Evan Dana L received a grant of 20,880 shares of Common Stock in the form of restricted stock units (RSUs) at no cash cost.
All RSUs vest in a single installment on the earlier of the day before Upwork’s 2027 annual stockholder meeting or June 4, 2027, subject to continued service, bringing the director’s direct holdings to 56,835 shares.
HARVEY KEVIN reported acquisition or exercise transactions in this Form 4 filing.
Upwork, Inc. director Kevin Harvey received two equity awards of common stock on June 4, 2026, totaling 6,207 and 20,880 restricted stock units granted at no cash cost, with vesting tied to continued service through dates in 2026–2027. After these grants he holds 147,216 shares directly and 2,565,307 shares indirectly through an entity he controls and a family trust.
Upwork, Inc. GM & Chief Operating Officer Anthony Ray Kappus reported routine equity compensation activity involving RSUs and a related tax sale. On May 18, 2026, 5,114 shares of common stock were acquired upon the conversion of restricted stock units at a price of $0.00 per share. On the same date, 1,905 shares of common stock were sold at a weighted average price of $8.6634 per share, within a range of $8.57 to $8.73 per share, to cover tax withholding obligations under a mandatory “sell to cover” arrangement, which the footnotes state was not a discretionary trade. After these transactions, Kappus directly holds 3,209 shares of common stock and 76,719 restricted stock units that each represent a right to receive one share of common stock, vesting in equal quarterly installments over four years beginning on May 18, 2026, subject to continued employment.
Upwork CFO Erica Gessert reported routine equity transactions involving RSU vesting, tax withholding, and resulting share ownership. She sold 22,162 shares of common stock at a weighted average price of $8.6634 per share in an open-market transaction that, according to the disclosure, was required to cover tax withholding obligations from RSU vesting rather than a discretionary trade.
On the same date, she exercised restricted stock units that converted into a total of 46,024 shares of common stock (8,524 shares from one RSU grant and 37,500 shares from another). After these transactions, she held 332,646 shares of common stock directly, while continuing to hold RSU awards that vest over time under quarterly schedules described in the disclosure.
Upwork, Inc.’s President & CEO Hayden Brown reported both stock sales and equity vesting activity. On May 18, 2026, she sold a total of 72,546 shares of common stock in open‑market transactions, including 50,000 shares at a weighted average price of $8.5695 per share and 22,546 shares at $8.6634 per share. Footnotes state that part of these sales were required "sell to cover" transactions to fund tax withholding on vesting restricted stock units, and that one sale was executed under a pre‑arranged Rule 10b5‑1 plan adopted on November 19, 2025, indicating the timing was not fully discretionary.
On the same date, Brown exercised or converted 46,822 restricted stock units into common stock at a conversion price of $0.00, in three tranches of 13,638, 18,334 and 14,850 RSUs, following quarterly vesting schedules tied to continued employment. A footnote also notes 1,544 shares acquired through the company’s employee stock purchase plan on May 14, 2026. The share balances reported after these transactions show that she continues to hold a substantial direct equity position in Upwork.
Kappus Anthony Ray reported acquisition or exercise transactions in this Form 4 filing.
Upwork, Inc. executive Anthony Ray Kappus, GM & Chief Operating Officer, received a compensation grant of 22,603 restricted stock units (RSUs). Each RSU represents a contingent right to receive one share of Upwork common stock.
The RSUs vest in equal quarterly installments over four years beginning on July 18, 2026, as long as Kappus remains employed with Upwork on each vesting date. Following this grant, his reported direct holdings of RSUs total 22,603 units.
Upwork, Inc. Chief Accounting Officer Sabrina Mekhalfa reported routine equity compensation activity. She exercised restricted stock units into 3,577 shares of common stock, then sold 1,482 shares at a weighted average price of $12.3121 per share to cover tax withholding obligations under a mandatory “sell to cover” arrangement, which the company’s plan requires and is not a discretionary trade. Following these transactions, she holds 2,095 shares of common stock directly and 39,352 restricted stock units that vest in equal quarterly installments over three years beginning on March 18, 2026, subject to continued employment.
Upwork, Inc. Chief Financial Officer Erica Gessert reported routine equity compensation activity involving restricted stock units and common stock. On March 18, 2026, she exercised restricted stock units covering 8,433 and 9,699 shares, receiving the same number of common shares at a conversion price of $0.00 per share.
On the same date, 9,278 shares of common stock were sold at a weighted average price of $12.312 per share, pursuant to a mandatory “sell to cover” arrangement to satisfy tax withholding obligations, as required under Upwork’s equity incentive plans. Following these transactions, Gessert directly held 307,240 shares of common stock. The restricted stock units vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to her continued employment.
UPWORK, INC President & CEO Hayden Brown reported routine equity compensation activity. On March 18, 2026, Brown exercised restricted stock units that converted into a total of 46,410 shares of common stock at an exercise price of $0.00 per share.
To cover tax withholding obligations from these RSU vestings, 23,745 shares of common stock were sold in a mandated “sell to cover” transaction at a weighted average price of $12.3118 per share, which the footnotes state was not a discretionary trade. Following these transactions, Brown directly owned 798,732 shares of Upwork common stock. The RSUs vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to continued employment.
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, 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.
Upwork Inc. (UPWK) disclosed that its President & CEO, who is also a director, reported selling 60,000 shares of common stock on 11/21/2025. The shares were sold at a weighted average price of $18.2019 per share, with individual trade prices ranging from $18.08 to $18.22. After this transaction, the reporting person beneficially owns 1,047,894 shares of Upwork common stock, held directly. The filer has committed to provide detailed trade breakdowns upon written request to the company, its shareholders, or the SEC staff.
Upwork Inc. director reports stock sale in a Form 4 filing. On 11/21/2025, the reporting person, a director of Upwork, Inc. (UPWK), sold 12,500 shares of common stock in an open-market transaction. The weighted average sale price was $17.5079 per share, with individual trades executed between $17.40 and $17.62 per share. Following this sale, the director beneficially owns 85,129 shares of Upwork common stock held directly.
Upwork Inc. (UPWK) President & CEO reported multiple equity transactions on 11/18/2025 tied to restricted stock units (RSUs). Several RSU awards vested and were converted into common stock, including 9,589, 7,610, 14,850, and 18,333 shares, all at an exercise price of $0.00 per share. Following these transactions, the reporting person directly owned 1,107,894 shares of common stock and held additional RSUs covering 9,589, 7,611, 74,250, and 91,667 shares.
To cover tax withholding obligations from the RSU vesting, the CEO sold 12,114 shares at a weighted average price of $16.1385 and 12,732 shares at a weighted average price of $17.2405. The filing states these sales were mandated "sell to cover" transactions under Upwork’s equity incentive plans and do not represent discretionary trades by the executive. The RSUs vest over time based on continued employment, with various schedules beginning on February 18, 2023, May 18, 2022, February 18, 2024, and May 18, 2023.
Upwork Inc. (UPWK) filed a Form 4 reporting equity transactions by its Chief Financial Officer. On 11/18/2025, 37,500 restricted stock units (RSUs) vested and were converted into the same number of common shares. These RSUs were part of an award that began vesting 25% on May 18, 2024, with additional vesting in equal quarterly installments.
To cover tax withholding obligations from this vesting, the CFO had 9,059 shares sold at a weighted average price of $16.1382 per share and 9,434 shares sold at a weighted average price of $17.2402 per share under a mandated “sell to cover” arrangement, which the filing states was not a discretionary trade. Following these transactions, the CFO directly owned 237,612 shares of Upwork common stock and held 225,000 RSUs representing contingent rights to receive an equal number of shares.
Upwork Inc. (UPWK) executive GM, Marketplace reported several equity transactions. On November 17, 2025, the reporting person sold 561 shares of common stock at $16.45 per share under a Rule 10b5-1 trading plan. On November 18, 2025, 3,750 restricted stock units (RSUs) were converted into common shares, and the person then sold 955 shares at a weighted average price of $16.1426 and 1,047 shares at a weighted average price of $17.2393. On November 19, 2025, an additional 1,748 shares were sold at a weighted average price of $18.1293.
Some of the sales were required to cover tax withholding obligations tied to RSU vesting, described as “sell to cover” transactions rather than discretionary trades. Following these transactions, the reporting person directly owned 345 shares of Upwork common stock and 18,750 RSUs, each RSU representing one share that vests quarterly over four years beginning on May 18, 2023.