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sellWeak cluster of 4

Erica Gessert sold $263k of UPWK

Chief Financial Officer at UPWORK, INC. 19,036 shares at an average of $13.84, traded Aug 18, 2025, filed Aug 20, 2025.

Warning score
35
Value
$263k
19,036 shares
Holdings after
209,202
-8% from before
From 52-week low
+52%
low $9.20, close $13.99
From 52-week high
-20%
high $17.50, as of Aug 18, 2025

Score components

  • Role
    CFO
    +22
  • Trade size
    $263k at market
    +13
  • Share of holdings sold
    Sold 8.3% of holdings
    0
  • Cluster
    4 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 +41.2%, 3m +27.8%, 6m -3.4%.

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 Aug 20, 2025: -39.5%SPY +23.6% · excess -63.1%

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 0001562180-25-005925, as filed. Open on EDGAR

DateTransactionSharesPriceValueHoldings afterFiled
Aug 18, 2025MOption exercise
Common Stock
+37,500--228,238Aug 20, 2025
Aug 18, 2025SOpen-market sale
Common Stock
-19,036$13.84$263k209,202Aug 20, 2025
Aug 18, 2025MOption exercise
Restricted Stock Unitsderivative
-37,500$0.00$0262,500Aug 20, 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.

Erica Gessert sold $263k of UPWK | InsiderTell