Upwork (NASDAQ:UPWK) General Manager, Marketplace Dave Bottoms completed insider sales totaling 32,662 shares of common stock in two separate transactions on February 18 and February 19, 2026, generating roughly $446,254 in proceeds. The transactions were carried out at price ranges reported as $13.34 to $14.085 on one day and $13.28 to $13.79 on the other, with the detailed trades recorded at specific per-share prices of $13.802 and $13.5115.
On February 18, Bottoms sold 17,013 shares at $13.802 per share, producing proceeds of approximately $234,813. The following day, February 19, he sold 15,649 shares at $13.5115 per share, yielding around $211,441. Company filings indicate the purpose of these dispositions was to satisfy tax withholding obligations arising from the vesting of Restricted Stock Units (RSUs) or Performance Stock Units (PSUs).
Part of the February 19 transaction was executed under a pre-established Rule 10b5-1 trading plan that Bottoms adopted on May 30, 2025. The use of a 10b5-1 plan is documented in the filings and applies to at least the second day of the reported sales.
Earlier in the same week, Bottoms exercised option-based awards tied to performance and restricted stock units. On February 17 he exercised options to acquire 28,912 shares of common stock, and on February 18 he exercised options to acquire 3,750 shares. After accounting for the exercises and subsequent sales to cover withholding, filings show Bottoms directly owns 345 shares of Upwork common stock.
Market context for the timing of the sales is notable. Upwork shares were trading at $13.32 at the referenced time, down 33% year-to-date and trading close to the 52-week low of $11.13. InvestingPro analysis cited within filings and commentary describes the stock as appearing undervalued at current prices, with the company holding a market capitalization of $1.73 billion and a price-to-earnings ratio of 16.
Corporate capital allocation moves also feature in the company’s recent disclosure. Upwork announced a new $300 million share repurchase program, which adds to its existing authorizations and brings the total repurchase capacity to $600 million since November 2023. The company previously deployed $136 million in 2025 to repurchase more than 9 million shares.
Analyst reactions have been varied despite the buyback activity. Goldman Sachs trimmed its price target to $27 but left a Buy rating intact, citing a growth outlook in the face of fourth-quarter revenue and adjusted EBITDA that met or slightly exceeded the high end of guidance. UBS lowered its target to $23 while maintaining a Buy rating, pointing to revenue and EBITDA beats that were narrower than expected. RBC Capital reduced its price target to $20 and kept a Sector Perform rating, citing concerns related to higher execution risk and the expected trajectory of performance during the year.
These analyst adjustments reflect differing assessments of Upwork’s near-term execution and recovery path even as the company continues repurchase activity. The insider sales were explicitly attributed to tax-withholding needs from equity vesting and a portion tied to a pre-arranged trading plan, while option exercises increased Bottoms’ holdings immediately prior to the share dispositions. Filings show the post-transaction direct ownership level for Bottoms at 345 shares.