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sellWeak

Anthony Ray Kappus sold $5,053 of UPWK

GM & Chief Operating Officer at UPWORK, INC. 558 shares at an average of $9.06, traded Jul 18, 2026, filed Jul 21, 2026.

Warning score
10
Value
$5,053
558 shares
Holdings after
4,063
-12% from before
From 52-week low
+16%
low $7.84, close $9.06
From 52-week high
-59%
high $22.11, as of Jul 17, 2026

Score components

  • Role
    COO
    +20
  • Trade size
    $5k at market
    0
  • Share of holdings sold
    Sold 12% of holdings
    +5
  • Cluster
    No other insider selling within 14 days
    0
  • 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.

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 Jul 21, 2026: -6.4%SPY +4.2% · excess -10.7%

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 0001860481-26-000014, as filed. Open on EDGAR

DateTransactionSharesPriceValueHoldings afterFiled
Jul 18, 2026MOption exercise
Common Stock
+1,412--4,621Jul 21, 2026
Jul 18, 2026SOpen-market sale
Common Stock
-558$9.06$5,0534,063Jul 21, 2026
Jul 18, 2026MOption exercise
Restricted Stock Unitsderivative
-1,412$0.00$021,191Jul 21, 2026

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%
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%
20Weak
UPWKsell 3
UPWORK, INC
Sabrina Mekhalfa
Chief Accounting Officer
$10k
1,276 shares
-22%

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.

Anthony Ray Kappus sold $5,053 of UPWK | InsiderTell