Upwork's CEO Sold Nearly $7 Million in Company Stock. Is This a Warning Sign for Shareholders?

Hayden Brown, President & CEO of Upwork (NASDAQ:UPWK), disclosed the sale of 350,000 shares in multiple open-market transactions on November 25, 2025 and November 26, 2025; see the SEC Form 4 filing for details.

Transaction summary

Transaction value based on SEC Form 4 weighted average purchase price ($19.51); post-transaction value based on November 26, 2025 market close ($19.51).

Key questions

• How significant was the transaction relative to Hayden Brown's direct holdings?
  The 350,000 shares sold represented 33.4% of Ms. Brown's direct holdings immediately prior to the transaction, a substantial reduction compared to the historical median sell trade of 30,672 shares (2.19% of holdings per trade in the past year).
• Did the transaction exhaust Ms. Brown's available direct ownership or leave a meaningful residual stake?
  After the transaction, Ms. Brown retained 697,894 shares directly, valued at approximately $13.7 million as of November 26, 2025, which accounts for 0.53% of Upwork's outstanding shares based on the latest reported figures.
• How does the transaction compare to Ms. Brown's historical selling patterns?
  Over the past year, Ms. Brown made 15 sell trades with a median size of 40,000 shares for sell-only events and 28,741 shares across all trade events, making this 350,000-share sale the largest single disposition in the observed period and well above both medians.
• Was there any notable movement in Upwork's stock price around the transaction dates?
  Upwork shares closed at $19.58 on November 26, 2025, with the weighted average sale price at $19.51 per share; the stock posted a one-year total return of 16.3% as of the transaction date.

Company overview

* 1-year price change calculated using November 26, 2025 as the reference date.

Company snapshot

• Upwork provides an online work marketplace connecting businesses with independent professionals and agencies across a wide range of categories, including sales, marketing, IT, and creative services.
• The company generates revenue primarily through service fees charged to clients and freelancers for facilitating talent sourcing, contracting, collaboration, and payment processing on its platform.
• Upwork targets enterprises, small and medium-sized businesses, and individual entrepreneurs seeking flexible, remote, and specialized talent globally.

Upwork, Inc. operates at scale as a leading online staffing and employment services platform, leveraging technology to streamline remote talent engagement for businesses worldwide. The company’s strategic focus on digital marketplace efficiency and secure payment solutions positions it as a key enabler in the evolving flexible workforce landscape.

Upwork's broad talent pool and comprehensive platform functionalities offer a competitive edge in serving diverse client needs across industries.

Foolish take

CEO Hayden Brown's sale of 350,000 shares in Upwork is noteworthy because it's a significant portion of her holdings. The company's stock hit a 52-week high of $20.54 in September, and remained elevated at the time of her sale. This suggests Ms. Brown was taking advantage of this to capture some gains.

Hayden Brown continues to own nearly 700,000 Upwork shares, so her November disposition isn't necessarily a red flag for shareholders to sell. That said, the substantial size of her sale understandably raises concerns.

So far, Upwork is experiencing respectable performance in 2025. It reached record quarterly revenue of $201.7 million in the third quarter, representing a 4% year-over-year increase. Its Q3 net income rose 6% year over year to $29.3 million.

The company expects full-year 2025 revenue to range between $782 million and $787 million, which is an increase over 2024's $769.3 million. This is a positive sign, although not spectacular sales growth.

Upwork stock's price-to-earnings ratio of about 11 hovers near a high point for 2025, signifying shares are on the pricey side. This indicates now is a good time to sell, which may have contributed to Hayden Brown's large disposition. However, in terms of whether to buy, the earnings multiple signals now is not a good time to pick up shares.

Glossary

Open-market transaction: The buying or selling of securities on a public exchange, not through private agreements.
SEC Form 4: A required filing disclosing insider trades by company officers, directors, or significant shareholders.
Weighted average purchase price: The average price paid per share, weighted by the number of shares in each transaction.
Direct ownership: Shares held personally and directly by an individual, not through trusts or indirect means.
Outstanding shares: The total number of a company's shares currently held by all shareholders.
Disposition: The act of selling or otherwise transferring ownership of an asset or security.
Total return: The investment's price change plus all dividends and distributions, assuming those payouts are reinvested.
Service fees: Charges collected by a platform for facilitating transactions or providing services to users.
Talent sourcing: The process of finding and recruiting skilled professionals for specific roles or projects.
Payment processing: Handling and transferring payments between parties, often through a secure online system.
TTM: The 12-month period ending with the most recent quarterly report.

Robert Izquierdo has positions in Upwork. The Motley Fool has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy.