NASDAQ:UPWK

Upwork Stock Insider Trading

Industrials > Staffing & Employment Services

Buy UPWK

*Your capital is at risk

$8.56

-0.420 (-4.68%)

At Close: Jun 03, 2026

Upwork Stock Insider Power

Based on the 100 latest insides trades, we have calculated the insider power to be negative at -65.48. In total, the insiders bought 1.83M and sold 820.13K UPWK shares in the last 100 trades. The insider score can be negative despite buy/sell ratio being positive. The score focuses on the quality of the trades.

Insider Power (Last 100 transactions)	-65.48
● Buy	1.83M shares
● Sell	820.13K shares
76% Buy Activity Weak Negative Correlation
Buy Signal Low Confidence Apr 17, 2026 Analysis Breakdown: Signal is highly questionable due to a strongly contradictory negative Insider Power Score of -65.48. Confidence increased due to high data reliability score of 100. Supported by overwhelming buy-side pressure (76% buys).

Historical Insider Trades

Date	Type	Person	Role	Amount
May 18, 2026 Buy	Restricted Stock Units M-Exempt	Brown Hayden President & CEO	CEO / President	18 334 Value: $160.4K
May 18, 2026 Buy	Restricted Stock Units M-Exempt	Gessert Erica Chief Financial Officer	C-Suite Officer	8 524 Value: $74.6K
May 18, 2026 Buy	Restricted Stock Units M-Exempt	Brown Hayden President & CEO	CEO / President	14 850 Value: $129.9K
May 18, 2026 Buy	Restricted Stock Units M-Exempt	Brown Hayden President & CEO	CEO / President	13 638 Value: $119.3K
May 18, 2026 Buy	Common Stock M-Exempt	Brown Hayden President & CEO	CEO / President	13 638 Value: $119.3K
May 18, 2026 Buy	Common Stock M-Exempt	Brown Hayden President & CEO	CEO / President	18 334 Value: $160.4K
May 18, 2026 Sell	Common Stock S-Sale	Brown Hayden President & CEO	CEO / President	22 546 Value: $195.3K
May 18, 2026 Buy	Common Stock M-Exempt	Brown Hayden President & CEO	CEO / President	14 850 Value: $129.9K
May 18, 2026 Sell	Common Stock S-Sale	Brown Hayden President & CEO	CEO / President	50 000 Value: $428.5K
May 18, 2026 Buy	Restricted Stock Units M-Exempt	Kappus Anthony Ray Gm & Chief Operating Officer	C-Suite Officer	5 114 Value: $44.7K
May 18, 2026 Buy	Common Stock M-Exempt	Kappus Anthony Ray Gm & Chief Operating Officer	C-Suite Officer	5 114 Value: $44.7K
May 18, 2026 Sell	Common Stock S-Sale	Kappus Anthony Ray Gm & Chief Operating Officer	C-Suite Officer	1 905 Value: $16.5K
May 18, 2026 Buy	Common Stock M-Exempt	Gessert Erica Chief Financial Officer	C-Suite Officer	8 524 Value: $74.6K
May 18, 2026 Buy	Common Stock M-Exempt	Gessert Erica Chief Financial Officer	C-Suite Officer	37 500 Value: $328.1K
May 18, 2026 Sell	Common Stock S-Sale	Gessert Erica Chief Financial Officer	C-Suite Officer	22 162 Value: $192.0K
May 18, 2026 Buy	Restricted Stock Units M-Exempt	Gessert Erica Chief Financial Officer	C-Suite Officer	37 500 Value: $328.1K
Apr 18, 2026 Buy	Restricted Stock Units A-Award	Kappus Anthony Ray Gm & Chief Operating Officer	C-Suite Officer	22 603 Value: $193.5K
Apr 17, 2026 Buy	No securities beneficially owned	Kappus Anthony Ray Gm & Chief Operating Officer	C-Suite Officer	0 Value: $0
Apr 17, 2026 Buy	Restricted Stock Units	Kappus Anthony Ray Gm & Chief Operating Officer	C-Suite Officer	81 833 Value: $922.3K
Mar 19, 2026 Sell	Common Stock S-Sale	Bottoms Dave Gm, Marketplace	Officer	7 000 Value: $80.4K
Mar 18, 2026 Buy	Common Stock M-Exempt	Bottoms Dave Gm, Marketplace	Officer	8 980 Value: $108.6K
Mar 18, 2026 Sell	Common Stock S-Sale	Bottoms Dave Gm, Marketplace	Officer	11 575 Value: $142.5K
Mar 18, 2026 Buy	Common Stock M-Exempt	Bottoms Dave Gm, Marketplace	Officer	6 024 Value: $72.8K
Mar 18, 2026 Buy	Restricted Stock Units M-Exempt	Bottoms Dave Gm, Marketplace	Officer	8 980 Value: $108.6K
Mar 18, 2026 Buy	Common Stock M-Exempt	Bottoms Dave Gm, Marketplace	Officer	5 904 Value: $71.4K

About Insider Power

Insider Power is a proprietary algorithm developed by StockInvest.us to evaluate the significance of insider transactions. The calculation considers the size, type, and timing of transactions, as well as the insider’s role within the company.

It is important to note that, in general, there is little to no correlation between insider transactions and short-term stock price movements. In one of our studies, only 0.22%^* of stocks with insider activity showed a measurable correlation — and even then, it was unclear whether the effect was caused by insider actions or simply by the stock’s broader trend.

While our algorithms are designed to highlight potentially meaningful signals, these cannot be regarded as statistically significant on their own. Insider trading activity should therefore be seen as informative rather than as direct trading guidance. The Insider Power metric was created to present this information in a clearer and more accessible way, helping investors better understand the possible context of insider activity.

* October 6th, 2025 - Tested on 5562 stocks

ABOUT UPWORK INC.

Upwork Inc., together with its subsidiaries, operates a work marketplace that connects businesses with various independent professionals and agencies in the United States, India, the Philippines, and internationally. The company's work marketplace provides access to talent with various skills across a range of categories, including sales and marketing, customer service, data science and analytics, design and creative, web, mobile, and software de...

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