Insider Selling: Upwork (NASDAQ:UPWK) CAO Sells 1,482 Shares of Stock

Key Points

  • CFO Erica Gessert sold 9,278 Upwork shares on March 18 at an average price of $12.31 for roughly $114,212, trimming her stake by about 2.93% to 307,240 shares.
  • Multiple senior insiders have also sold stock recently (including the CEO and a director), creating selling pressure even as the board authorized a $300 million share buyback program to repurchase up to ~18% of outstanding shares.

Upwork Inc. (NASDAQ:UPWK - Get Free Report) CAO Sabrina Mekhalfa sold 1,482 shares of the stock in a transaction that occurred on Wednesday, March 18th. The stock was sold at an average price of $12.31, for a total transaction of $18,243.42. Following the transaction, the chief accounting officer directly owned 2,095 shares in the company, valued at approximately $25,789.45. This represents a 41.43% decrease in their position. The transaction was disclosed in a document filed with the Securities & Exchange Commission, which is available through this hyperlink.

Upwork Stock Down 0.7%

Shares of UPWK opened at $11.27 on Friday. Upwork Inc. has a fifty-two week low of $11.09 and a fifty-two week high of $22.84. The company's fifty day moving average is $15.88 and its two-hundred day moving average is $17.52. The firm has a market cap of $1.47 billion, a PE ratio of 13.42 and a beta of 1.07.

Upwork declared that its Board of Directors has authorized a stock repurchase program on Wednesday, February 18th that permits the company to repurchase $300.00 million in outstanding shares. This repurchase authorization permits the company to purchase up to 18% of its shares through open market purchases. Shares repurchase programs are often a sign that the company's management believes its stock is undervalued.

Key Headlines Impacting Upwork




Here are the key news stories impacting Upwork this week:

  • Negative Sentiment: CEO Hayden Brown sold 23,745 shares at an average of $12.31 (~$292K), a 2.9% reduction in her stake — a notable insider sale from the company’s top executive. CEO Hayden Brown SEC Filing
  • Negative Sentiment: CFO Erica Gessert sold 9,278 shares at ~$12.31 (~$114K), reducing her position by ~2.9% — another senior officer sale. CFO Erica Gessert SEC Filing
  • Negative Sentiment: CAO Sabrina Mekhalfa sold 1,482 shares at ~$12.31 (~$18K), cutting her stake by ~41%. CAO Sabrina Mekhalfa SEC Filing
  • Negative Sentiment: Director/insider Dave Bottoms reported two recent sales (11,575 shares at $12.31 and 7,000 shares at $11.49), significantly reducing his holdings. Multiple insider dispositions amplify the perception of insider-led selling. Dave Bottoms SEC Filings
  • Negative Sentiment: Media and analyst coverage is bearish: headlines report shares “plummet” and note analysts are resetting valuations and expectations for Upwork, which can pressure sentiment and trigger further selling. Reddit and Upwork Shares Plummet, What You Need To Know
  • Negative Sentiment: Analysis piece discusses a shifting Upwork story as analysts cut forecasts and valuations — a catalyst for downgrades and lower price targets. Why The Upwork (UPWK) Story Is Shifting

Wall Street Analyst Weigh In

Several equities research analysts recently issued reports on UPWK shares. Scotiabank dropped their price target on shares of Upwork from $17.00 to $15.00 and set a "sector perform" rating on the stock in a research note on Tuesday, February 10th. UBS Group decreased their price target on shares of Upwork from $26.00 to $23.00 and set a "buy" rating for the company in a research report on Tuesday, February 10th. Royal Bank Of Canada reduced their price objective on shares of Upwork from $24.00 to $20.00 and set a "sector perform" rating on the stock in a research note on Tuesday, February 10th. Jefferies Financial Group upped their target price on shares of Upwork from $22.00 to $27.00 and gave the company a "buy" rating in a research note on Monday, January 5th. Finally, Zacks Research lowered Upwork from a "strong-buy" rating to a "hold" rating in a research report on Monday, February 2nd. Seven analysts have rated the stock with a Buy rating and six have assigned a Hold rating to the company's stock. According to data from MarketBeat, the company has a consensus rating of "Moderate Buy" and an average price target of $22.60.

Read Our Latest Stock Analysis on UPWK

Institutional Trading of Upwork

Several hedge funds have recently made changes to their positions in the stock. Royal Bank of Canada grew its stake in Upwork by 68.9% during the 1st quarter. Royal Bank of Canada now owns 191,587 shares of the company's stock worth $2,501,000 after buying an additional 78,123 shares during the last quarter. MIRAE ASSET GLOBAL ETFS HOLDINGS Ltd. increased its holdings in shares of Upwork by 5.1% in the 1st quarter. MIRAE ASSET GLOBAL ETFS HOLDINGS Ltd. now owns 74,466 shares of the company's stock worth $972,000 after acquiring an additional 3,599 shares during the period. Millennium Management LLC lifted its position in Upwork by 364.0% in the 1st quarter. Millennium Management LLC now owns 789,638 shares of the company's stock valued at $10,305,000 after purchasing an additional 619,459 shares during the last quarter. UBS AM A Distinct Business Unit of UBS Asset Management Americas LLC grew its position in Upwork by 10.2% in the 1st quarter. UBS AM A Distinct Business Unit of UBS Asset Management Americas LLC now owns 338,680 shares of the company's stock worth $4,420,000 after purchasing an additional 31,378 shares during the last quarter. Finally, Creative Planning increased its stake in shares of Upwork by 16.9% in the second quarter. Creative Planning now owns 29,239 shares of the company's stock valued at $393,000 after purchasing an additional 4,230 shares during the period. Institutional investors own 77.71% of the company's stock.

About Upwork

(Get Free Report)

Upwork Inc operates a leading online talent marketplace that connects businesses with independent professionals worldwide. Through its digital platform, the company enables clients across industries—including technology, marketing, creative services and customer support—to source, hire and manage freelance talent on demand. Key features of the Upwork platform include streamlined job posting, proposal evaluation, time-tracking tools, invoicing and secure payment processing, all designed to simplify collaboration between clients and remote workers.

The company traces its roots to the merger of two pioneering freelance marketplaces, Elance (founded in 1998) and oDesk (founded in 2003), which combined in 2015 to form a unified entity.

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