Upwork executive Dave Bottoms sells stock for $52,769

Dave Bottoms, GM of Marketplace at Upwork , Inc. (NASDAQ:UPWK), recently sold shares of the company’s stock as reported in a Form 4 filing with the SEC. The transactions occurred on May 15 and May 19, 2025. The freelance marketplace platform, currently valued at $2.18 billion, maintains impressive gross profit margins of 77.8% and shows strong financial health according to InvestingPro analysis.

On May 15, Bottoms sold 1,009 shares at a price range between $17.06 and $17.27, totaling approximately $17,294. A few days later, on May 19, he sold an additional 2,130 shares, priced between $16.50 and $16.84, for a total of about $35,475. The stock, which has gained over 43% in the past year, currently trades at an attractive P/E ratio of 9.4x.

These sales were conducted under a Rule 10b5-1 plan, which allows company insiders to set up a trading plan for selling stocks they own. The plan was adopted on June 7, 2023, and modified on May 28, 2024.

Additionally, on May 18, Bottoms acquired 3,750 shares through the exercise of restricted stock units (RSUs), which were part of his compensation package. These RSUs were converted to common stock at no cost, and the shares were used to cover tax obligations related to the vesting of these units.

In other recent news, Upwork Inc. reported a record revenue of $192.7 million for the first quarter of 2025, marking a 1% year-over-year increase and surpassing market expectations. The company’s earnings before interest, taxes, depreciation, and amortization (EBITDA) reached $56 million, reflecting a 29% margin, which was 16% higher than anticipated. JMP Securities analysts maintained their Market Outperform rating for Upwork, with a price target of $18, highlighting the company’s strong financial performance and strategic advantages. Meanwhile, Citi analysts adjusted their outlook, reducing Upwork’s price target from $19 to $18 while maintaining a Neutral stance, citing ongoing macroeconomic factors as a concern.

Upwork’s Gross Services Volume (GSV) was reported at $988 million, a slight decline of 2% year-over-year but still above consensus expectations. The company’s focus on AI and enterprise strategies contributed to a 25% year-over-year increase in AI-related GSV. Upwork launched the Ooma (NYSE:OOMA) AI platform, which has boosted user engagement and proposal writing, further enhancing the platform’s efficiency. The company set its full-year 2025 revenue guidance between $740 million and $760 million, with adjusted EBITDA expected to range from $190 million to $200 million.

Despite some challenges at the beginning of the sales funnel, Upwork’s diverse range of services across 58 categories is seen as a strategic advantage. The integration of AI technology is expected to boost liquidity and conversion rates on the platform. Upwork’s guidance for the second half of 2025 remains cautious, yet it suggests a continued positive trajectory. Analysts from JMP Securities project that the company is on course to achieve 35% EBITDA margins in the coming years.

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