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sellModerate cluster of 510b5-1 plan

Michael Massaro sold $2.1M of FLYW

Chief Executive Officer at Flywire Corp. 112,500 shares at an average of $18.39, traded Sep 1, 2026, filed Sep 3, 2026.

Warning score
45
Value
$2.1M
112,500 shares
Holdings after
2,400,558
-4% from before
From 52-week low
-
no price yet
From 52-week high
-
no price yet

Score components

  • Role
    CEO
    +25
  • Trade size
    $2.1M at market
    +25
  • Share of holdings sold
    Sold 4.5% of holdings
    0
  • Cluster
    5 insiders selling within 14 days
    +15
  • 10b5-1 plan
    Pre-scheduled under a 10b5-1 plan
    -20

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.

FLYWOct 9, 2026 · close 18.76
Since filing Sep 3, 2026: +0.3%SPY +0.9% · excess -0.6%

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 0001628280-26-060411, as filed. Open on EDGAR

DateTransactionSharesPriceValueHoldings afterFiled
Sep 1, 2026FTax withholding
Voting Common Stock10b5-1
-39,993$18.19$727k2,513,05839 d ago
Sep 1, 2026SOpen-market sale
Voting Common Stock10b5-1
-112,500$18.39$2.1M2,400,55839 d ago

Related signals

Other insiders at Flywire Corp and this insider’s other filings.

ScoreCompanyInsiderValueHoldingsFiled
35Weak
FLYWsell 510b5-1
Flywire Corp
David R. King
See Remarks
$660k
36,900 shares
-13%
22Weak
FLYWsell 510b5-1
Flywire Corp
Peter Butterfield
General Counsel and CCO
$219k
12,156 shares
-2%
23Weak
FLYWsell 510b5-1
Flywire Corp
Mohit Kansal
Chief Payments Officer
$232k
12,423 shares
-3%
50Moderate
FLYWsell 5
Flywire Corp
Voss Capital, LP
owner
$841k
44,768 shares
-0%
5Weak
FLYWsell10b5-1
Flywire Corp
Peter Butterfield
General Counsel and CCO
$118k
9,009 shares
-2%
33Weak
FLYWbuy
Flywire Corp
Voss Capital, LP
owner
$275k
25,000 shares
+1%
7Weak
FLYWsell10b5-1
Flywire Corp
Peter Butterfield
General Counsel and CCO
$200k
13,327 shares
-3%
40Moderate
FLYWbuy
Flywire Corp
Voss Capital, LP
owner
$3.2M
226,112 shares
+2%
0Weak
FLYWsell 210b5-1
Flywire Corp
Phillip John Riese
director
$7,007
467 shares
-0%
5Weak
FLYWsell10b5-1
Flywire Corp
Peter Butterfield
General Counsel and CCO
$111k
8,120 shares
-2%

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.

Michael Massaro sold $2.1M of FLYW | InsiderTell