Early Access — free while we kick the tires
EdgarHawk

Brown Hayden

President & CEO

Director Officer

Latest: President & CEO selling · May 2026

9 filings analyzed · 1 company · Latest 2026-05-20

Companies

Company Buys Sells Direction
UPWORK, INC UPWK 0 39 Net selling

Activity

May 2026
2026-05-20 UPWORK, INC UPWK
low
Sell
72,546 shares
$623,800
Significance 3/10

Brown Hayden (CEO) sells 72,546 shares for $623,800.02 via scheduled 10b5-1 plan on 2026-05-18 at blended $8.60.

Brown Hayden executed two separate sales totaling 72,546 shares for $623,800.02 under a pre-arranged 10b5-1 trading plan adopted on 2025-11-19. The sales occurred at prices of $8.66 and $8.57 per share. His holdings remain substantial at 774,552 shares post-transaction, representing an 8.6% reduction. At the current price of $8.66, the stock is trading -62.1% from its 52-week high of $22.84 and has declined 21.9% over 30 days and 35.0% over 90 days. The underlying business carries a P/E of 9.84 with $195.5M in quarterly revenue and $31.5M in net income, though annual revenue growth has slowed to 2.4%. Because this transaction is governed by a scheduled 10b5-1 plan rather than discretionary execution, the sales reflect predetermined scheduling rather than market-responsive decision-making.

February 2026
2026-02-19 UPWORK, INC UPWK
medium
Sell
123,152 shares
$1,698,959
Significance 5/10

Brown Hayden (CEO) sold 123,152 shares for $1.7M at $13.80; stock down 31.7% in 30 days

Brown Hayden executed 2 separate sales totaling 123,152 shares for $1,698,958.53 at a blended average price of $13.80 on 2026-02-18, reducing his holdings by 13.7%. The transaction occurs against a backdrop of significant recent price weakness: the stock trades at $13.32, down 31.7% over 30 days and 39.8% from its 52-week high of $22.11. Examining Hayden's same-ticker history at UPWK, his most recent 5 prior trades show mixed timing outcomes—3 recent November 2025 sells were followed by 30-day gains (6.0% to 13.2%), suggesting those sales preceded temporary rebounds, though one earlier 90-day outcome showed -26.8% (well-timed). His cross-ticker track record across 18 prior sells shows an average 90d return of -4.3% with a 53.33% well-timed rate. The timing of this sale—following steep recent declines but at prices near current levels—does not carry an obvious forward predictive signal. Fundamentals remain modest: P/E of 11.79, 2.4% annual revenue growth, and $29.3M net income on $201.7M revenue, suggesting the valuation compression may reflect market disappointment in growth rather than material operational deterioration.

November 2025
2025-11-28 UPWORK, INC UPWK
medium
Sell
350,000 shares
$6,827,478
Significance 6/10

UPWK CEO Brown Hayden sold 350,000 shares (33.4% of holdings) for $6,827,477.50 in 3 transactions; stock now +28.3% over 90 days.

Brown Hayden, President & CEO of Upwork, executed 3 separate sales totaling 350,000 shares for $6,827,477.50 on 2025-11-25 and 2025-11-26 at an average price of $19.51, reducing his holdings by 33.4% from 1,047,894 to 697,894 shares. The current price of $19.74 is near the transaction price and only -1.6% from the 52-week high, while the stock has gained 28.3% over the past 90 days—timing that is inconsistent with his prior track record at this ticker, where 0 of 5 measurable prior sells achieved negative 90-day returns (the criterion for well-timed sales). His cross-ticker track record shows a 70.00% well-timed sell rate with -7.1% average 90-day return, yet at UPWK specifically his recent sells have posted -19.0%, -15.5%, -14.7%, and -10.0% 30-day returns. The size and concentration of this 350K-share sale—occurring amid strong company fundamentals (11.6% revenue growth, P/E of 10.44, net income of $29,335,000.00 in the latest quarter)—and the continued strength in the stock price merit attention to whether this reflects insider positioning ahead of a potential near-term shift.

2025-11-25 UPWORK, INC UPWK
medium
Sell
60,000 shares
$1,092,114
Significance 4/10

Upwork CEO Brown Hayden sold 60,000 shares at $18.20 on 2025-11-21 (now $19.69); holding 1.05M shares post-sale.

Brown Hayden sold 60,000 shares (5.4% of his pre-transaction holdings) at $18.20, capturing $1,092,114.00 in total value at a price approximately 1.9% below the 52-week high of $20.07. Across his cross-ticker open-market sell history, his 90-day well-timed rate is 70.00%, but at Upwork specifically, his 5 prior sells show no measurable negative 90-day outcomes (outcomes remain pending on the most recent trades). The stock has gained 23.1% over 30 days and 33.0% over 90 days leading into this sale. Upwork's fundamentals include $201.7M in latest-quarter revenue, $29.3M net income, and an 11.6% annual revenue growth rate at a P/E of 10.42, suggesting a company in sustained growth with a modest valuation multiple.

September 2025
2025-09-19 UPWORK, INC UPWK
high
Sell
82,344 shares
$1,568,198
Significance 6/10

Brown Hayden (CEO) sold 82,344 shares in 4 transactions over 3 days for $1,568,198.18; post-transaction holdings 1,082,358 shares.

Brown Hayden conducted 4 separate sales totaling 82,344 shares for $1,568,198.18 between 2025-09-17 and 2025-09-19, reducing his stake by 7.1% to 1,082,358 shares remaining. The blended average sale price of $19.04 comes as UPWK approaches its 52-week high of $20.07, with the stock up 41.3% over the prior 30 days and 52.7% over 90 days. His prior 5 trades at this ticker show mixed timing results, with 3 measurable 90-day outcomes all well-timed (negative returns, confirming he sold before declines), while his most recent two August sales have not yet shown measurable 90-day results despite strong 30-day gains. His broader cross-ticker track record shows an 87.50% well-timed rate on sells with average 90-day underperformance of -14.3%, indicating a consistent pattern of exiting positions ahead of pullbacks. The near-peak timing of this sale, following sustained momentum and within a context of strong recent price performance, aligns with his demonstrated historical pattern of selling into strength.

August 2025
2025-08-19 UPWORK, INC UPWK
high
Sell
85,577 shares
$1,179,313
Significance 8/10

UPWK CEO Brown Hayden sells 85,577 shares for $1.2M; all 5 prior UPWK sales were well-timed (90d declines), now at 52-week low territory

Brown Hayden, President & CEO, executed 2 separate sales totaling 85,577 shares for $1,179,312.91 on 2025-08-15 and 2025-08-18 at a blended average price of $13.78. This represents a 7.1% reduction in his holdings to 1,118,291 shares. The current price of $13.86 is only 0.6% above transaction price, but the stock is -20.8% from its 52-week high of $17.50 and recently declined 14.6% over 90 days. Notably, across his 5 prior open-market sales at UPWK, all were well-timed at the 90-day mark, with a consistent pattern of -16.7% to -19.4% declines in the months following those sales. Given the stock's current technical positioning and this insider's demonstrated pattern of well-timed exits at this specific ticker, this filing warrants close attention to whether near-term momentum turns negative.

May 2025
2025-05-19 UPWORK, INC UPWK
high
Sell
86,438 shares
$1,467,833
Significance 6/10

UPWK CEO Brown Hayden sold 86,438 shares across 5 transactions for $1,467,832.62; stock up 29.9% in 30d but down 1.9% in 90d

Brown Hayden, President & CEO of Upwork, conducted 5 separate sales totaling 86,438 shares for $1,467,832.62 on 2025-05-15 and 2025-05-19, reducing his position by 7.1% from 1,217,229 shares to 1,130,791 shares. The blended average sale price of $16.98 is slightly above the current price of $16.55, and the sales occurred against a backdrop of strong near-term momentum: the stock rose 29.9% over the prior 30 days before falling 1.9% over 90 days. Across his cross-ticker track record, Hayden's prior sells have been well-timed at the 90-day horizon (100.00% well-timed rate), though at this specific ticker (UPWK), only 1 of 1 prior measurable 90-day outcomes was well-timed. The company's fundamentals remain solid—$192.7M quarterly revenue, +11.6% annual growth, and a P/E of 9.30—leaving open whether the sales reflect a view on near-term valuation, portfolio balance, or personal liquidity needs.

2025-05-09 UPWORK, INC UPWK
medium
Sell
40,000 shares
$636,956
Significance 5/10

CEO Brown Hayden sold 40,000 UPWK shares at $15.92; still holds 1.18M shares post-sale.

Brown Hayden, President & CEO, sold 40,000 shares of UPWORK at $15.92 on 2025-05-07 for $637.0K, reducing his holdings by 3.3% to 1,183,741 shares. At the time of sale, the stock was trading -3.5% from its 52-week high of $17.49; it has since risen 27.9% over the past 30 days to a current price of $16.88. Hayden's prior sell on 2025-03-07 at the same ticker resulted in a 30-day decline of -16.4%, while his earlier sale on 2024-02-20 saw a 90-day decline of -10.0%, indicating a 100% well-timed rate at the 90-day mark for UPWK. His cross-ticker track record shows 2 prior sells with an average 90-day return of -10.0% and a 90% well-timed rate, suggesting consistent ability to exit ahead of weakness. The current stock price of $16.88 remains 6.1% below the 2025-05-07 sale price, and the company's fundamentals show strong profitability with $192.7M in latest quarterly revenue, $37.7M net income, and a P/E of 9.48.

March 2025
2025-03-11 UPWORK, INC UPWK
high
Sell
60,000 shares
$851,946
Significance 6/10

CEO Brown Hayden sells 60,000 UPWK shares at $14.20; stock down 23.4% from 52-week high, now at $13.39

Brown Hayden, President & CEO, sold 60,000 shares (60.0K shares) of UPWORK at $14.20 on 2025-03-07, reducing his holdings from 1,275,083 shares to 1,215,083 shares (-4.7% of pre-transaction holdings). The sale occurred against a backdrop of significant recent weakness: the stock is trading at $13.39, down 23.4% from its 52-week high of $17.49 and down 15.1% over the past 30 days. Notably, Hayden's cross-ticker insider track record shows a 100.00% well-timed rate on his 1 prior sell, with a 90-day return of -10.0% after that transaction, indicating his prior sales have preceded subsequent declines. At the company level, fundamentals remain solid with $193.8M in revenue, $27.8M net income, and 11.6% annual growth, with a P/E of 7.12 suggesting valuation is not stretched. The timing of this sale amid significant recent drawdown, combined with his strong historical pattern of selling before further declines, warrants attention to whether this signals emerging concerns or is isolated portfolio rebalancing.

Related insiders

Create a free account

Build watchlists, get email alerts on the tickers you follow, and read the full AI analysis on every insider filing.

Sign up — free during early access