Massaro Michael 4

What Happened Michael Massaro, Chief Executive Officer of Flywire Corp (FLYW), sold a total of 50,000 shares on May 6, 2026 in two transactions: 11,830 shares at a reported weighted average price of $15.65 (proceeds $185,190) and 38,170 shares at a reported weighted average price of $16.62 (proceeds $634,496). Total proceeds from the sales were approximately $819,686. The sales were open-market or private sales executed pursuant to a previously adopted Rule 10b5-1 trading plan.

Key Details

• Transaction date: May 6, 2026.
• Reported prices and ranges:
  • 11,830 shares — weighted avg $15.65 (individual trade prices ranged $15.085 to $16.00) [F2].
  • 38,170 shares — weighted avg $16.62 (individual trade prices ranged $16.15 to $16.905) [F3].
• Total proceeds: ~$819,686.
• Shares owned after the transactions: Not specified in the supplied summary (see the Form 4 for "ownership following reported transaction" details).
• Notable footnotes: Sales were made under a Rule 10b5-1 plan [F1]. Portions of reported holdings are held in trusts (M Massaro Trust and Michael P. Massaro 2021 Irrevocable Trust) where the reporting person disclaims beneficial ownership [F4, F5].
• Filing: Form 4 was filed May 8, 2026 (two days after the transactions), which is within the typical Section 16 reporting window.

Context Sales under a 10b5-1 plan are pre-arranged and commonly used by insiders to sell shares on a scheduled basis; such sales are often routine and do not necessarily indicate a change in the insider’s view of the company. For retail investors, purchases generally convey more direct insider confidence than sales; this filing documents routine disposition of shares by the CEO rather than a new purchase or option exercise.