Hayden Brown Sells 123,152 Shares of Upwork (NASDAQ:UPWK) Stock

Upwork Inc. (NASDAQ:UPWK) CEO Hayden Brown sold 123,152 shares of the stock in a transaction on Wednesday, February 18th. The stock was sold at an average price of $13.80, for a total value of $1,699,497.60. Following the sale, the chief executive officer directly owned 776,067 shares in the company, valued at approximately $10,709,724.60. This trade represents a 13.70% decrease in their ownership of the stock. The transaction was disclosed in a filing with the SEC, which is available through this link.

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

Upwork Trading Down 1.1%

Shares of Upwork stock opened at $13.17 on Friday. The company has a market cap of $1.72 billion, a PE ratio of 15.68 and a beta of 1.06. The company has a 50 day moving average of $19.03 and a 200-day moving average of $17.72. Upwork Inc. has a 1-year low of $11.13 and a 1-year high of $22.84.

Upwork announced that its Board of Directors has authorized a share buyback plan on Wednesday, February 18th that allows the company to repurchase $300.00 million in outstanding shares. This repurchase authorization allows the company to buy up to 18% of its shares through open market purchases. Shares repurchase plans are generally an indication that the company’s board believes its stock is undervalued.

Trending Headlines about Upwork

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 Trading of Upwork

A number of institutional investors and hedge funds have recently bought and sold shares of the stock. Royal Bank of Canada lifted its holdings 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 period. MIRAE ASSET GLOBAL ETFS HOLDINGS Ltd. raised its position in shares of Upwork by 5.1% during the first 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 last quarter. Millennium Management LLC lifted its stake in shares of Upwork by 364.0% in the first quarter. Millennium Management LLC now owns 789,638 shares of the company’s stock worth $10,305,000 after acquiring an additional 619,459 shares during the period. UBS AM A Distinct Business Unit of UBS Asset Management Americas LLC boosted its holdings in Upwork by 10.2% in the first quarter. UBS AM A Distinct Business Unit of UBS Asset Management Americas LLC now owns 338,680 shares of the company’s stock valued at $4,420,000 after acquiring an additional 31,378 shares during the last quarter. Finally, VIRGINIA RETIREMENT SYSTEMS ET Al acquired a new stake in Upwork during the 2nd quarter valued at approximately $211,000. 77.71% of the stock is currently owned by institutional investors and hedge funds.

Wall Street Analyst Weigh In

Several analysts recently weighed in on UPWK shares. Canaccord Genuity Group set a $22.00 price objective on Upwork in a research report on Tuesday, February 10th. Royal Bank Of Canada lowered their target price on Upwork from $24.00 to $20.00 and set a “sector perform” rating for the company in a research note on Tuesday, February 10th. Citizens Jmp restated a “market outperform” rating and issued a $27.00 price target on shares of Upwork in a research note on Wednesday, November 19th. Jefferies Financial Group upped their price objective on shares of Upwork from $22.00 to $27.00 and gave the stock a “buy” rating in a research report on Monday, January 5th. Finally, Weiss Ratings reissued a “hold (c+)” rating on shares of Upwork in a research note on Wednesday, January 21st. Seven equities research analysts have rated the stock with a Buy rating and six have assigned a Hold rating to the stock. Based on data from MarketBeat.com, Upwork has an average rating of “Moderate Buy” and an average price target of $22.60.

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.