Upwork CFO Erica Gessert sells $78,896 in shares

Upwork CFO Erica Gessert divested 9,336 shares of the company's common stock on September 18, 2026, generating $78,896 in proceeds. The transaction, aimed at fulfilling tax obligations related to the vesting of RSUs, occurred at a weighted average price of $8.4508, with individual trades between $8.315 and $8.52 per share. Gessert's shares were trading at $8.15, reflecting a 58.9% decline year-to-date and proximity to a 52-week low of $7.44.

Despite Upwork's stock appearing undervalued, trading with a P/E ratio of 10.7, the company faced challenges from AI automation and macroeconomic pressures. On the same day, Gessert increased her holdings by acquiring an additional 8,433 shares and 9,700 RSUs, totaling 373,586 shares directly owned. The RSUs vest quarterly, with the most recent acquisition set to vest starting June 18, 2025.

Upwork's second-quarter 2026 earnings surpassed expectations with $0.41 EPS on $191.7 million revenue, but the company lowered its full-year revenue guidance amid AI automation and search performance concerns. Industry analysts, including Canaccord, RBC Capital, Scotiabank, and Needham, slashed price targets due to ongoing headwinds, with Canaccord targeting $9.00 and Needham at $11.00, maintaining a Buy rating.