Insider transaction details
On March 18, 2026, Upwork Inc. Chief Financial Officer Erica Gessert sold 9,278 shares of the company’s common stock for an aggregate amount of about $114,230. The shares were sold at prices ranging between $12.13 and $12.52 per share.
Concurrent equity acquisition
On the same day as the sale, Gessert acquired 18,132 shares through the exercise of restricted stock units. Both actions - the open-market sale and the RSU exercise - were recorded for March 18, 2026.
Price context and valuation note
Upwork's shares were trading near a 52-week low at the time of the transaction. The stock's 52-week low is $11.13 and the most recent quoted price was $11.28, representing a decline of more than 43% over the last six months. According to InvestingPro analysis cited alongside these transactions, the stock appears undervalued at current levels, with a Fair Value estimate that suggests potential upside from prevailing market prices.
Corporate capital actions
Separately, the company announced a new $300 million share repurchase program. That addition brings Upwork's total authorized repurchases to $600 million since November 2023. The company has deployed $136 million in 2025 to repurchase in excess of 9 million shares, reflecting ongoing share buyback activity.
Recent financial performance and analyst response
Upwork's fourth-quarter 2025 results showed revenue and adjusted EBITDA at or slightly above the high end of the company’s prior guidance range. Following those results, UBS and Goldman Sachs each reduced their price targets for the company to $23 and $27, respectively, while both lenders retained a Buy opinion on the stock.
Management change and separation terms
In leadership news, David T. Bottoms, General Manager, Marketplace, has agreed to resign, with employment continuing through April 3. Under his separation agreement he will receive a lump-sum payment equal to twelve months of his base salary and COBRA insurance premium reimbursements for up to twelve months.
Contextual note
These transactions and corporate moves - insider stock activity, an expanded repurchase program, quarterly results, analyst target adjustments, and an executive departure - were disclosed contemporaneously and reflect the company's recent operational and capital allocation developments.
Key points
- Upwork CFO Erica Gessert sold 9,278 shares for about $114,230 and exercised RSUs for 18,132 shares on March 18, 2026.
- The company added a $300 million repurchase program, taking total repurchase authorizations to $600 million since November 2023, after deploying $136 million in 2025 to buy back over 9 million shares.
- Q4 2025 revenue and adjusted EBITDA came in at or slightly above the high end of guidance; UBS and Goldman Sachs trimmed price targets to $23 and $27 while keeping Buy ratings.
Risks and uncertainties
- Stock price weakness - Upwork's shares are trading near a 52-week low and have fallen more than 43% over six months, which may reflect market concerns about valuation or performance.
- Analyst target reductions - Despite Buy ratings, lowered price targets from UBS and Goldman Sachs introduce uncertainty around near-term upside expectations.
- Leadership transition - The resignation of the GM, Marketplace and the associated separation payments create short-term management and execution risk.