Insider Selling: Upwork (NASDAQ:UPWK) CFO Sells $114,212.18 in Stock

Upwork Inc. (NASDAQ:UPWK) CFO Erica Gessert sold 9,278 shares of Upwork stock in a transaction dated Wednesday, March 18th. The stock was sold at an average price of $12.31, for a total value of $114,212.18. Following the completion of the sale, the chief financial officer directly owned 307,240 shares of the company’s stock, valued at approximately $3,782,124.40. This trade represents a 2.93% decrease in their position. The sale was disclosed in a legal filing with the SEC, which can be accessed through the SEC website.

Erica Gessert also recently made the following trade(s):

• On Wednesday, February 18th, Erica Gessert sold 26,292 shares of Upwork stock. The shares were sold at an average price of $13.80, for a total transaction of $362,829.60.

Upwork Stock Down 0.7%

Shares of NASDAQ:UPWK opened at $11.27 on Monday. The firm has a market capitalization of $1.47 billion, a PE ratio of 13.42 and a beta of 1.08. The company has a 50-day moving average price of $15.88 and a two-hundred day moving average price of $17.54. Upwork Inc. has a twelve month low of $11.09 and a twelve month high of $22.84.

Upwork announced that its Board of Directors has approved a share buyback plan on Wednesday, February 18th that allows the company to buyback $300.00 million in outstanding shares. This buyback authorization allows the company to purchase up to 18% of its stock through open market purchases. Stock buyback plans are generally a sign that the company’s management believes its stock is undervalued.

Upwork News Summary

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

Analysts Set New Price Targets

A number of equities research analysts have issued reports on the stock. Needham & Company LLC reissued a “buy” rating and set a $25.00 target price on shares of Upwork in a report on Tuesday, February 10th. Scotiabank cut their price target on Upwork from $17.00 to $15.00 and set a “sector perform” rating for the company in a report on Tuesday, February 10th. Weiss Ratings reiterated a “hold (c+)” rating on shares of Upwork in a research note on Wednesday, January 21st. The Goldman Sachs Group reissued a “buy” rating and set a $27.00 price objective on shares of Upwork in a report on Tuesday, February 10th. Finally, Zacks Research downgraded Upwork from a “strong-buy” rating to a “hold” rating in a research note on Monday, February 2nd. Seven research analysts have rated the stock with a Buy rating and six have issued a Hold rating to the company’s stock. According to MarketBeat.com, the stock has a consensus rating of “Moderate Buy” and an average price target of $22.60.

Institutional Inflows and Outflows

Several institutional investors have recently modified their holdings of the stock. Accredited Wealth Management LLC raised its stake in Upwork by 5,280.0% in the third quarter. Accredited Wealth Management LLC now owns 1,345 shares of the company’s stock valued at $25,000 after purchasing an additional 1,320 shares in the last quarter. Farther Finance Advisors LLC grew its stake in Upwork by 594.4% in the 4th quarter. Farther Finance Advisors LLC now owns 1,361 shares of the company’s stock worth $27,000 after buying an additional 1,165 shares in the last quarter. Clearstead Advisors LLC grew its stake in Upwork by 998.4% in the 3rd quarter. Clearstead Advisors LLC now owns 1,406 shares of the company’s stock worth $26,000 after buying an additional 1,278 shares in the last quarter. Fifth Third Bancorp increased its holdings in shares of Upwork by 2,405.7% in the 3rd quarter. Fifth Third Bancorp now owns 1,754 shares of the company’s stock worth $33,000 after buying an additional 1,684 shares during the last quarter. Finally, GAMMA Investing LLC increased its holdings in shares of Upwork by 379.2% in the 4th quarter. GAMMA Investing LLC now owns 1,840 shares of the company’s stock worth $36,000 after buying an additional 1,456 shares during the last quarter. 77.71% of the stock is currently owned by institutional investors.

About Upwork

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.