Insider Selling: Upwork (NASDAQ:UPWK) Insider Sells 15,649 Shares of Stock

February 20, 2026 by InsiderTrades.com

Key Points

Upwork CEO Hayden Brown sold 123,152 shares on Feb. 18 at an average price of $13.80 for roughly $1.70M, cutting her stake by 13.7% to 776,067 shares, according to an SEC filing.
The Board approved a $300 million share buyback program, authorizing repurchases of up to about 18% of outstanding shares, a move typically signaling the board views the stock as undervalued.
Shares traded near $13.31 mid-day (52‑week range $11.13–$22.84); analysts have a consensus "Moderate Buy" with a $22.60 target and institutional investors hold roughly 77.7% of the stock.

Upwork Inc. (NASDAQ:UPWK - Get Free Report) insider Dave Bottoms sold 15,649 shares of the stock in a transaction on Thursday, February 19th. The stock was sold at an average price of $13.51, for a total value of $211,417.99. Following the completion of the transaction, the insider directly owned 345 shares of the company's stock, valued at approximately $4,660.95. The trade was a 97.84% decrease in their position. The transaction was disclosed in a filing with the SEC, which is available at the SEC website.

MarketBeat Week in Review – 12/15 - 12/19

Dave Bottoms also recently made the following trade(s):

On Wednesday, February 18th, Dave Bottoms sold 17,013 shares of Upwork stock. The shares were sold at an average price of $13.80, for a total value of $234,779.40.
On Friday, December 19th, Dave Bottoms sold 9,622 shares of Upwork stock. The shares were sold at an average price of $20.66, for a total transaction of $198,790.52.
On Thursday, December 18th, Dave Bottoms sold 11,285 shares of Upwork stock. The stock was sold at an average price of $20.59, for a total transaction of $232,358.15.

Upwork Trading Up 0.5%

UPWK traded up $0.07 on Friday, reaching $13.39. The company had a trading volume of 950,317 shares, compared to its average volume of 3,775,252. The company has a market capitalization of $1.75 billion, a P/E ratio of 15.96 and a beta of 1.06. The company has a fifty day moving average of $19.21 and a 200-day moving average of $17.71. Upwork Inc. has a one year low of $11.13 and a one year high of $22.84.

Can Upwork Maintain Its Comeback? Reasons to Be Bullish and Bearish

Upwork announced that its Board of Directors has authorized a share repurchase program on Wednesday, February 18th that authorizes the company to repurchase $300.00 million in shares. This repurchase authorization authorizes the company to repurchase up to 18% of its shares through open market purchases. Shares repurchase programs are generally an indication that the company's management believes its stock is undervalued.

Institutional Inflows and Outflows

Large investors have recently bought and sold shares of the business. Price T Rowe Associates Inc. MD boosted its position in Upwork by 44.2% during 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 acquiring an additional 5,893,970 shares during the period. Boston Partners lifted its position in shares of Upwork by 785.7% in the third quarter. Boston Partners now owns 2,322,575 shares of the company's stock worth $42,962,000 after purchasing an additional 2,060,356 shares in the last quarter. Summit Partners Public Asset Management LLC purchased a new stake in shares of Upwork in the fourth quarter worth approximately $40,136,000. Invenomic Capital Management LP acquired a new stake in shares of Upwork during the third quarter worth approximately $24,782,000. Finally, LSV Asset Management grew its position in Upwork by 22.1% during the second 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 in the last quarter. 77.71% of the stock is owned by institutional investors and hedge funds.

Analyst Ratings Changes

Upwork's Stock Soars on Q3 Blowout and a New AI Blueprint

Several brokerages recently commented on UPWK. Roth Mkm boosted their target price on Upwork from $22.00 to $23.00 and gave the stock a "buy" rating in a report on Tuesday, February 10th. Jefferies Financial Group lifted their price target on Upwork from $22.00 to $27.00 and gave the company a "buy" rating in a research report on Monday, January 5th. Canaccord Genuity Group set a $22.00 price objective on Upwork in a report on Tuesday, February 10th. The Goldman Sachs Group reaffirmed a "buy" rating and set a $27.00 target price on shares of Upwork in a research note on Tuesday, February 10th. Finally, Zacks Research lowered Upwork from a "strong-buy" rating to a "hold" rating in a report on Monday, February 2nd. Seven equities research analysts have rated the stock with a Buy rating and six have given a Hold rating to the company's stock. Based on data from MarketBeat, Upwork presently has a consensus rating of "Moderate Buy" and a consensus price target of $22.60.

Get Our Latest Report on UPWK

Key Headlines Impacting Upwork

Here are the key news stories impacting Upwork this week:

Positive Sentiment: Board authorizes a flexible $300 million share repurchase (authorizes buybacks of up to ~18% of outstanding stock), a material capital-return program that can reduce float and boost EPS over time. Article Title
Positive Sentiment: Market reaction: coverage notes shares rose on the buyback news (investor sentiment is lifting near-term demand). Article Title
Neutral Sentiment: Analyst and institutional context is mixed — consensus remains a modestly positive “moderate buy” with a long-run average target above current levels, and institutions hold ~78% of shares; analysts’ ratings/targets vary so the buyback may prompt revisions but not unanimous upgrades.
Negative Sentiment: Significant insider selling this week: CEO Hayden Brown sold 123,152 shares (~$1.7M at ~$13.80), CFO and other insiders also sold portions of their positions—these large disposals can be read as a cautionary signal by some investors. SEC filings for the CEO sale are available here: SEC Filing
Negative Sentiment: Technicals and liquidity: shares remain well below the 50-day moving average and volume today is thin versus average, which raises the risk of volatile moves despite the buyback announcement.

Upwork Company Profile

(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.