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Upwork NASDAQ:UPWK Chief Financial Officer Erica Gessert sold a total of 18,493 shares of common stock on November 18, 2025, netting approximately $308,840. The sales were executed in two transactions, with prices ranging from $16.1382 to $17.2402. Upwork currently trades at $17.17 with a market capitalization of $2.21 billion and boasts impressive gross profit margins of 77.8%.
The filing with the Securities and Exchange Commission shows that the sales were to cover tax withholding obligations related to the vesting of restricted stock units (RSUs). These sales are mandated by Upwork’s equity incentive plans and do not represent discretionary trades by Gessert.
On the same day, Gessert also exercised options to acquire 37,500 shares of Upwork common stock through the conversion of 37,500 Restricted Stock Units. InvestingPro data shows Upwork trading at a low P/E ratio of 9.8 and is currently considered undervalued according to InvestingPro’s Fair Value analysis.
Following these transactions, Gessert directly owns 237,612 shares of Upwork. The company maintains a "GREAT" financial health score according to InvestingPro, which offers 10 more ProTips and a comprehensive Pro Research Report on Upwork among 1,400+ US equities.
In other recent news, Upwork Inc. has been the focus of several analyst updates following its Investor Day presentation. The company announced ambitious growth targets, including a projected annualized revenue growth of 13-15% and Adjusted EBITDA growth of approximately 20% through 2028. This suggests potential revenue of $1.13-$1.20 billion by 2028. Analysts have responded positively, with Goldman Sachs raising its price target for Upwork to $28, maintaining a Buy rating, and Canaccord Genuity increasing its target to $24 from $22, also with a Buy rating. Citizens reiterated its Market Outperform rating, highlighting growth catalysts such as AI-platform improvements and enterprise expansion. RBC Capital maintained its Sector Perform rating and a $21 price target, focusing on Upwork’s position in the fractionalized work market. These developments underscore the company’s strategic emphasis on artificial intelligence and enterprise solutions as key growth drivers.
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