Insider Selling: Upwork (NASDAQ:UPWK) CEO Sells $1,699,497.60 in Stock

Upwork Inc. (NASDAQ:UPWK) CEO Hayden Brown sold 123,152 shares of the firm’s stock in a transaction dated Wednesday, February 18th. The shares were sold at an average price of $13.80, for a total value of $1,699,497.60. Following the sale, the chief executive officer owned 776,067 shares in the company, valued at $10,709,724.60. The trade was a 13.70% decrease in their position. The transaction was disclosed in a filing with the Securities & Exchange Commission, which is available at the SEC website.

Hayden Brown also recently made the following trade(s):

• On Thursday, December 18th, Hayden Brown sold 23,147 shares of Upwork stock. The stock was sold at an average price of $20.59, for a total value of $476,596.73.
• On Tuesday, November 25th, Hayden Brown sold 75,000 shares of Upwork stock. The shares were sold at an average price of $19.78, for a total value of $1,483,500.00.
• On Wednesday, November 26th, Hayden Brown sold 275,000 shares of Upwork stock. The stock was sold at an average price of $19.43, for a total value of $5,343,250.00.
• On Friday, November 21st, Hayden Brown sold 60,000 shares of Upwork stock. The stock was sold at an average price of $18.20, for a total value of $1,092,000.00.

Upwork Stock Performance

UPWK stock opened at $13.17 on Friday. The company has a market capitalization of $1.72 billion, a PE ratio of 15.68 and a beta of 1.06. Upwork Inc. has a one year low of $11.13 and a one year high of $22.84. The company’s 50 day moving average price is $19.03 and its two-hundred day moving average price is $17.76.

Upwork declared that its board has approved a stock 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 reacquire up to 18% of its shares through open market purchases. Shares buyback plans are often an indication that the company’s board believes its shares are undervalued.

Key Upwork News

Here are the key news stories impacting Upwork this week:

• Positive Sentiment: Board authorizes a flexible $300 million buyback (authorizes repurchases of roughly 18% of shares), a meaningful capital‑return action that can reduce float and support EPS and investor sentiment. Globe and Mail: Buyback Announcement
• Positive Sentiment: Market reaction was initially positive — coverage notes shares rose on the buyback news, showing short‑term demand lift from the announcement. Investing.com: Market Reaction
• Neutral Sentiment: Analyst / institutional context is mixed: consensus is a modest “moderate buy” with an average target (~$22.60) well above the current price, and institutions own ~78% of the stock — the buyback may prompt revisions but not unanimous upgrades. MarketBeat: Analyst & Ownership Context
• Negative Sentiment: Significant insider selling this week: CEO Hayden Brown sold 123,152 shares (~$1.7M at ~$13.80); CFO Erica Gessert and other insiders (Dave Bottoms) also reduced positions — large insider disposals can be interpreted negatively by investors. SEC filings for the CEO sale are here and the InsiderTrades writeup for other insider sales is here. CEO SEC Filing InsiderTrades: Insider Sales
• Negative Sentiment: Technicals/liquidity are unfavorable near term: shares remain well below the 50‑day moving average and today’s volume is light versus average, increasing downside volatility risk despite the buyback. MarketBeat: Technicals

Institutional Inflows and Outflows

A number of hedge funds have recently bought and sold shares of UPWK. Price T Rowe Associates Inc. MD lifted its holdings in Upwork by 44.2% in the 4th quarter. Price T Rowe Associates Inc. MD now owns 19,231,377 shares of the company’s stock worth $381,166,000 after buying an additional 5,893,970 shares during the period. Boston Partners raised its holdings in shares of Upwork by 785.7% during the third quarter. Boston Partners now owns 2,322,575 shares of the company’s stock valued at $42,962,000 after acquiring an additional 2,060,356 shares in the last quarter. Summit Partners Public Asset Management LLC purchased a new stake in Upwork in the fourth quarter worth $40,136,000. Invenomic Capital Management LP bought a new stake in Upwork in the third quarter valued at $24,782,000. Finally, LSV Asset Management increased its position in Upwork by 22.1% during the 2nd quarter. LSV Asset Management now owns 6,534,575 shares of the company’s stock valued at $87,825,000 after purchasing an additional 1,183,169 shares during the period. Hedge funds and other institutional investors own 77.71% of the company’s stock.

Wall Street Analyst Weigh In

A number of research analysts have recently issued reports on UPWK shares. The Goldman Sachs Group reaffirmed a “buy” rating and set a $27.00 price objective on shares of Upwork in a research note on Tuesday, February 10th. BTIG Research restated a “neutral” rating on shares of Upwork in a report on Wednesday, November 19th. Royal Bank Of Canada reduced their price target on Upwork from $24.00 to $20.00 and set a “sector perform” rating on the stock in a research report on Tuesday, February 10th. Scotiabank lowered their price objective on Upwork from $17.00 to $15.00 and set a “sector perform” rating for the company in a research report on Tuesday, February 10th. Finally, Canaccord Genuity Group set a $22.00 price objective on Upwork in a research note on Tuesday, February 10th. Seven analysts have rated the stock with a Buy rating and six have issued a Hold rating to the company’s stock. According to data from MarketBeat, the stock has a consensus rating of “Moderate Buy” and a consensus price target of $22.60.

Upwork Company Profile

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.