Flywire (FLYW) CEO Michael Massaro Sells Shares

What Happened

• Michael Massaro, CEO of Flywire Corp (FLYW), disposed of a total of 152,493 shares on September 1, 2026. He sold 112,500 shares in an open-market sale for a weighted average price of $18.39 (proceeds reported as $2,068,684) and had 39,993 shares withheld to cover tax withholding on vested RSUs at $18.18 (value reported as $727,273). Combined proceeds/value are about $2.8 million.
• These actions are dispositions (sales/withholding) rather than purchases and are consistent with a scheduled/plan sale plus tax withholding on equity compensation.

Key Details

• Transaction dates: September 1, 2026; Form 4 filed Sept 3, 2026 (reports transactions on Sept 1).
• Open-market sale: 112,500 shares at a reported weighted average price of $18.39 (range $18.11–$18.77 across multiple trades).
• Tax withholding: 39,993 shares withheld at $18.18 to satisfy income tax obligations related to net-settled time-based RSUs (not an open-market sale).
• Total reported value: ~$2,795,957 (approximately $2.8M).
• Shares owned after transaction: Not specified in this filing.
• Notable footnotes: The open-market sale was made pursuant to a previously adopted Rule 10b5-1 trading plan (F2). Withheld shares represent tax remittance for RSU settlement and are not an open-market sale (F1). The reporting person disclaims beneficial ownership of certain shares held in trusts where the reporting person’s spouse is trustee (F4, F5).

Context

• The filing shows a scheduled/formulaic sale under a 10b5-1 plan plus tax-withholding on vested RSUs — a common pattern for executives monetizing vested equity and meeting tax obligations. The withheld shares were used solely to satisfy tax obligations (cashless/net settlement) and were not sold on the open market.
• No indication in the filing of late reporting; the Form 4 was filed two days after the transaction date (filed Sept 3 for Sept 1 transactions).