Upwork Inc. (NASDAQ: UPWK) reported an insider share sale by its chief financial officer, Erica Gessert, who sold 26,292 shares of the company’s common stock on February 18, 2026. According to the filing reporting the transaction, the sale generated approximately $362,887, with the per-share sale price recorded between $13.34 and $14.085. The company’s shares are currently trading at $13.32, reflecting a 33% decline year-to-date.
The same set of filings shows Gessert exercised stock options immediately prior to the sale. On February 17, she exercised options to acquire 40,477 shares, and on February 18 she exercised options to acquire an additional 37,500 shares. After accounting for these exercises and the subsequent sale, the disclosure lists Gessert as directly owning 298,386 shares of Upwork common stock.
Separately, the company has increased its buyback activity. Upwork announced a new $300 million share repurchase program, which raises the firm’s total authorized repurchase capacity to $600 million since November 2023. This new authorization follows the company’s deployment of $136 million in 2025 to repurchase more than 9 million shares.
On the operating front, Upwork’s fourth-quarter 2025 earnings results showed revenue and adjusted EBITDA coming in at or slightly above the high end of the guidance range the company provided. These results, combined with the expanded repurchase authorization, coincide with a range of analyst reactions. Goldman Sachs lowered its price target to $27 while maintaining a Buy rating. UBS moved its target to $23 and also kept a Buy rating. RBC Capital reduced its target to $20, citing higher execution risk but retaining a Sector Perform rating. Together these actions illustrate a mixed analyst outlook on the company’s near-term prospects.
The filing and corporate disclosures include an assessment that the company appears undervalued when measured against a Fair Value assessment conducted as part of a dedicated valuation analysis. For investors seeking additional detail on valuation nuances and related research, a comprehensive Pro Research Report is available.
The combination of insider option exercises, a subsequent sale, substantial buyback activity, and varied analyst revisions presents a layered picture for market participants monitoring Upwork. The insider transactions and corporate capital return decisions will be of particular interest to shareholders and to market observers assessing the stock’s valuation in the context of recent operational results.
Summary
Upwork’s CFO sold 26,292 shares for about $362,887 after exercising options that added 77,977 shares to her holdings. The company authorized an additional $300 million in share repurchases, bringing total buyback capacity to $600 million since November 2023, after repurchasing over 9 million shares for $136 million in 2025. Fourth-quarter 2025 revenue and adjusted EBITDA were at or slightly above the high end of guidance, while analysts have adjusted price targets in response to the company’s results and perceived execution risk.
Key Points
- Insider activity: CFO Erica Gessert sold 26,292 shares on February 18, 2026, for approximately $362,887, following exercises of options for 40,477 and 37,500 shares on February 17 and 18.
- Shareholder returns: Upwork authorized a new $300 million repurchase program, bringing total repurchase authorizations to $600 million since November 2023; the company repurchased over 9 million shares for $136 million in 2025.
- Operational and market signals: Q4 2025 revenue and adjusted EBITDA were at or slightly above guidance highs, while analysts trimmed price targets to $27, $23, and $20, reflecting divergent views on execution and valuation.
Risks and Uncertainties
- Price volatility risk: The stock is trading at $13.32 and is down 33% year-to-date, which may affect market perception of valuation and investor sentiment in the technology and online services sectors.
- Execution risk: At least one analyst cited higher execution risk when lowering their price target, indicating uncertainty around Upwork’s ability to sustain growth or margins, a concern for equity investors and corporate customers in the freelance platform market.
- Analyst outlook divergence: Differing analyst price target revisions create mixed expectations for the stock’s near-term direction, impacting capital markets participants assessing Upwork as an investment or trade candidate.