Upwork Inc. reported a flurry of insider activity and corporate actions on March 18, 2026, as President and Chief Executive Officer Hayden Brown both sold and acquired company stock and the board expanded share-repurchase capacity.
Insider transactions
On March 18, 2026, Brown sold 23,745 shares of Upwork common stock at an average sale price of $12.3118 per share, generating proceeds of approximately $292,343. The disposals occurred across multiple transactions with execution prices ranging from $12.13 to $12.52. That same day she exercised restricted stock units that resulted in the acquisition of 46,410 shares of Upwork common stock.
The market price at the time of reporting was $11.28, a level close to the security's 52-week low of $11.13.
Valuation and third-party commentary
An InvestingPro analysis referenced alongside the filings indicates the shares appear undervalued at current levels and notes a set of 15 additional ProTips available to subscribers, including commentary on the company’s strong financial health score. The InvestingPro note was presented as part of the reporting on the insider activity and valuation perspective.
Financial performance and capital allocation
Upwork disclosed fourth-quarter 2025 results in which revenue and adjusted EBITDA met or slightly exceeded the top end of the company's guidance. Following the release, analysts at Goldman Sachs and UBS reduced their price targets for the company to $27 and $23, respectively, though both firms maintained Buy ratings.
Concurrently, Upwork’s board approved a new $300 million share repurchase program. That authorization raises total buyback capacity to $600 million since November 2023. The company previously deployed $136 million in 2025 to repurchase more than 9 million shares.
Leadership change
Separately, Upwork announced the resignation of David T. Bottoms, who served as GM of Marketplace. Under a separation agreement, Mr. Bottoms will remain with the company through April 3 and will receive a lump-sum payment equal to twelve months of his base salary, plus reimbursement for COBRA insurance premiums for up to twelve months.
Taken together, the insider transactions, analyst moves, expanded repurchase plan and an executive departure illustrate a company navigating shareholder-return initiatives and leadership transitions while reporting quarterly results that met internal guidance.