Hayden Brown, President and Chief Executive Officer of Upwork, Inc. (NASDAQ:UPWK), filed a Form 4 on August 20, 2026, disclosing RSU conversions and two separate share dispositions that occurred on August 18, 2026.

Key Highlights

  • Three RSU tranches converted: Brown acquired 14,850, 18,333, and 13,639 shares of common stock through RSU vesting transactions coded "M" on August 18, 2026.
  • Tax-related sale: 23,241 shares were sold at a weighted average price of $8.4257, with individual transactions ranging from $8.37 to $8.45 per share, to satisfy mandatory tax withholding obligations.
  • Rule 10b5-1 plan sale: An additional 50,000 shares were sold at a weighted average price of $8.4271, ranging from $8.245 to $8.52 per share, under a plan adopted November 19, 2025.
  • Post-transaction ownership: Following all reported transactions, Brown directly held 771,076 shares of common stock.
  • Remaining RSUs: After the conversions, Brown's derivative holdings included 29,700, 36,667, and 190,944 RSUs remaining across the three respective tranches.

RSU Conversions, Mandatory Tax Sales, and Planned Disposition at Upwork

According to the filing, Brown's three RSU tranches each represent a contingent right to receive one share of Upwork common stock upon vesting. The three "M"-coded transactions on August 18, 2026 converted 14,850, 18,333, and 13,639 RSUs into common stock, sequentially bringing Brown's directly held share count from 812,345 to 830,678 and then to 844,317, per the reported running totals in Table I of the filing. Upwork, Inc. operates an online work marketplace connecting businesses with independent talent across a range of professional categories.

The filing notes that the 23,241-share sale was not a discretionary trade. Per the filing's explanation, it "represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs," and the sale "is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a 'sell to cover' transaction." This brought Brown's directly held total to 821,076 shares prior to the 10b5-1 plan sale.

The separate 50,000-share sale was made pursuant to a Rule 10b5-1 plan that Brown adopted on November 19, 2025, reducing directly held shares to 771,076. The filing was signed by Jacob McQuown as Attorney-in-Fact on August 20, 2026. Each of the three RSU tranches carries distinct vesting schedules: the first vests 25% on February 18, 2024, then 6.25% quarterly; the second vests in equal quarterly installments over four years beginning May 18, 2023; and the third vests in equal quarterly installments over four years beginning May 18, 2026.

What Was Disclosed

The filing reports three RSU-to-common-stock conversions, one mandatory tax-withholding sale of 23,241 shares, and one pre-planned sale of 50,000 shares, leaving Brown with 771,076 directly held shares of Upwork common stock as of August 18, 2026.