Upwork CFO’s Massive 40,000‑Share Buy Signals Insider Confidence Amid 31% Year‑to‑Date Decline

Insider Buying Spree Signals Confidence Amid Volatility

Upwork’s Chief Financial Officer, Erica Gessert, added 40,477 shares on February 17, 2026, a purchase that lifted her total holdings to 287,178. The buy coincided with a marginal dip in the stock price (–0.03 %) and a surge in social‑media buzz (238 % intensity), suggesting that the market is watching her moves closely. The transaction occurs just days after the company’s announcement that it will speak at the Citizens Technology Conference, a high‑profile event that could boost investor sentiment.

What the Recent Activity Means for Investors

Gessert’s latest purchase follows a pattern of disciplined buying. In the past year she has alternated between buying and selling shares and units, often selling tax‑withholding “sell‑to‑cover” transactions that are not discretionary. Her net exposure has remained positive, and her most recent trade is a clean, outright common‑stock purchase rather than a sell‑to‑cover or unit vesting. For investors, this signals a reaffirmation of belief in Upwork’s long‑term prospects, especially given the company’s strategic push into new professional‑services markets and its robust cash flow generation.

The broader insider landscape reinforces this sentiment. President Brown Hayden has executed 13 trades in the last week, largely buys that raise his stake to 899,219 shares. GM Bottoms Dave, meanwhile, has been buying and selling around 30,000 shares, balancing liquidity needs with a long‑term view. Together, the executive team’s activity paints a picture of confidence tempered by prudent liquidity management.

Gessert Erica: A Profile of Consistent Commitment

Gessert’s historic trade history shows a pattern of long‑term ownership. Since her first filing in December 2025, she has accumulated roughly 300,000 shares through a mix of direct purchases and RSU/PSU vesting. Her trades are often clustered around vesting dates, with a notable 40,477‑share purchase in February 2026 that aligns with a performance‑stock‑unit vesting event on December 31, 2025. Unlike some executives who frequently sell, Gessert’s trades are predominantly buy‑side, indicating a belief that Upwork’s valuation is still below its intrinsic value.

Her transaction cadence also reflects a strategic use of restricted stock units (RSUs) and performance stock units (PSUs). In 2025 she sold RSUs and PSUs in “sell‑to‑cover” transactions but never sold outright common shares except when the market price was favorable. This disciplined approach suggests she is focused on long‑term growth and shareholder value.

Implications for Upwork’s Future

The recent buying spree by Gessert and other insiders comes at a time when Upwork’s share price is down 31.66 % year‑to‑date, but the company’s valuation remains within its sector’s upper tier. With a price‑to‑earnings ratio of 14.3 and a price‑to‑book ratio of 2.74, investors are paying a modest premium for earnings and equity. The insider activity could be interpreted as a hedge against the stock’s recent volatility, signaling that management believes the company is poised for a recovery as it expands its service offerings and capitalizes on the growing remote‑work market.

For investors, Gessert’s recent buy is a positive cue, especially when combined with the company’s upcoming conference appearance and ongoing efforts to streamline operations. While Upwork’s share price remains under pressure, the insider confidence may help steady sentiment in the short term and position the stock for a rebound once the company delivers on its growth initiatives.