Skip to content
sellModerate cluster of 3

Hayden Brown sold $477k of UPWK

President & CEO at UPWORK, INC. 23,147 shares at an average of $20.59, traded Dec 18, 2025, filed Dec 22, 2025.

Warning score
43
Value
$477k
23,147 shares
Holdings after
721,158
-3% from before
From 52-week low
+74%
low $11.75, close $20.47
From 52-week high
-7%
high $21.95, as of Dec 18, 2025

Score components

  • Role
    CEO
    +25
  • Trade size
    $477k at market
    +18
  • Share of holdings sold
    Sold 3.1% of holdings
    0
  • Cluster
    3 insiders selling within 14 days
    +15
  • Exercise and sell
    Shares came from an option exercise in the same filing
    -15

What happened after comparable sells

Same side and tier, against the S&P 500, at 1, 3 and 6 months. Shown to Pro users; the whole table is on the backtest page.

This signal so far: 1m -7.5%, 3m -46.4%, 6m -63.2%.

Price around the trade, and since

From a quarter before the trade to today. The arrow is the trade, the circle the day the filing reached EDGAR, which is the first day anyone outside could act; the dotted line is the S&P 500 rebased to that day's close.

UPWKOct 9, 2026 · close 8.60
Since filing Dec 22, 2025: -59.6%SPY +14.5% · excess -74.1%

Daily candles, adjusted for splits and dividends. Green arrows are insider buys, red are sells, sized by value; the dashed line is the close on the filing day, the dotted line SPY rebased to it.Charts by TradingView Lightweight Charts™

Rows in this filing

Every transaction in Form 4 0001753662-25-000016, as filed. Open on EDGAR

DateTransactionSharesPriceValueHoldings afterFiled
Dec 18, 2025MOption exercise
Common Stock
+17,733--715,627Dec 22, 2025
Dec 18, 2025MOption exercise
Common Stock
+28,678--744,305Dec 22, 2025
Dec 18, 2025SOpen-market sale
Common Stock
-23,147$20.59$477k721,158Dec 22, 2025
Dec 18, 2025MOption exercise
Restricted Stock Unitsderivative
-17,733$0.00$0159,599Dec 22, 2025
Dec 18, 2025MOption exercise
Restricted Stock Unitsderivative
-28,678$0.00$0372,807Dec 22, 2025

Related signals

Other insiders at UPWORK, INC and this insider’s other filings.

ScoreCompanyInsiderValueHoldingsFiled
37Weak
UPWKsell 4
UPWORK, INC
Hayden Brown
President & CEO
$202k
23,893 shares
-3%
31Weak
UPWKsell 4
UPWORK, INC
Erica Gessert
Chief Financial Officer
$79k
9,336 shares
-2%
46Moderate
UPWKsell 4
UPWORK, INC
Anthony Ray Kappus
GM & Chief Operating Officer
$386k
45,732 shares
-37%
20Weak
UPWKsell 4
UPWORK, INC
Sabrina Mekhalfa
Chief Accounting Officer
$11k
1,299 shares
-16%
25Weak
UPWKsell 310b5-1
UPWORK, INC
Hayden Brown
President & CEO
$617k
73,241 shares
-9%
34Weak
UPWKsell 3
UPWORK, INC
Erica Gessert
Chief Financial Officer
$192k
22,844 shares
-6%
25Weak
UPWKsell 3
UPWORK, INC
Anthony Ray Kappus
GM & Chief Operating Officer
$17k
1,964 shares
-21%
10Weak
UPWKsell
UPWORK, INC
Anthony Ray Kappus
GM & Chief Operating Officer
$5,053
558 shares
-12%
37Weak
UPWKsell 3
UPWORK, INC
Hayden Brown
President & CEO
$191k
23,468 shares
-3%
30Weak
UPWKsell 3
UPWORK, INC
Erica Gessert
Chief Financial Officer
$75k
9,169 shares
-3%

Not investment advice. Scores and forward returns are decision support built from public SEC filings and past prices; they describe what happened after comparable filings, not what will happen after this one. Do your own research and size your risk.

Hayden Brown sold $477k of UPWK | InsiderTell