Massaro Michael 4
4 · Flywire Corp · Filed Feb 26, 2026
Research Summary
AI-generated summary of this filing
Flywire (FLYW) CEO Michael Massaro Receives RSU Award
What Happened
- Michael Massaro, CEO of Flywire (FLYW), was granted 751,811 restricted stock units (RSUs) on 2026-02-24 (no cash paid). The RSUs represent shares of common stock that will vest over time (see vesting schedule below).
- Separately, on 2025-12-24 the filing reports a transfer by gift of 465,043 shares from the Meredith E. Massaro Revocable Trust to Massaro for estate-planning purposes (no cash). The Form 4 lists the gift as an exempt transaction.
Key Details
- Transaction dates and prices:
- 2025-12-24: Gift of 465,043 shares — $0.00 (no consideration) (reported as exempt gift from family trust).
- 2026-02-24: Grant/award of 751,811 RSUs — $0.00 (award of equity, not an open-market purchase).
- Vesting for the 751,811 RSUs (per footnote): 25% vests on March 1, 2027; remaining shares vest in equal quarterly installments over the next three years, subject to continued service.
- Footnotes/ownership notes:
- The 465,043 gifted shares were transferred from the Meredith E. Massaro Revocable Trust; the trustee is Massaro’s spouse (footnotes F1, F2).
- Some shares referenced are held by other family trusts (Michael P. Massaro 2021 Irrevocable Trust) and the reporting person disclaims beneficial ownership of those trust-held shares except to the extent of any pecuniary interest (F5).
- The filing was adjusted to reflect 1,243 shares acquired under the company ESPP (F3).
- Filing timing: Form 4 was filed on 2026-02-26. The 2025-12-24 gift appears to have been reported late (filed more than two business days after the transaction); the 2026-02-24 RSU grant was filed within the typical 2-business-day window.
Context
- Gifts and grants recorded at $0 indicate no cash changed hands; gifts are often estate-planning moves and do not necessarily signal the insider’s view of the stock.
- RSU grants are common executive compensation; these RSUs vest over several years and are tied to continued service rather than an immediate sale. They are not immediate cash events unless/when vested shares are sold.
Insider Transaction Report
Form 4
Flywire CorpFLYW
Massaro Michael
DirectorChief Executive Officer
Transactions
- Gift
Voting Common Stock
[F1][F2]2025-12-24−465,043→ 192,193 total(indirect: See footnote) - Gift
Voting Common Stock
[F1][F3]2025-12-24+465,043→ 2,305,158 total - Award
Voting Common Stock
[F4][F3]2026-02-24+751,811→ 3,056,969 total
Holdings
- 307,548(indirect: See footnote)
Voting Common Stock
[F5]
Footnotes (5)
- [F1]The reported exempt transaction involves a transfer of securities by bona fide gift for estate planning purposes from the Meredith E. Massaro Revocable Trust dated November 1, 2017 (the "M Massaro Trust"), of which the Reporting Person's spouse is a trustee, to the Reporting Person for no consideration.
- [F2]The shares are held by the M Massaro Trust, of which the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16 or for any other purpose, except to the extent of the Reporting Person's pecuniary interests therein, if any.
- [F3]Adjusted to reflect 1,243 shares acquired under the Issuer's Employee Stock Purchase Plan.
- [F4]Represents shares of common stock underlying a time-based restricted stock unit award (RSU). The RSU vests with respect to 25% of the shares on March 1, 2027, with the remainder vesting in equal quarterly installments over the following three years, provided that the Reporting Person has provided continuous service to the Issuer through the applicable vesting date.
- [F5]The shares are held by the Michael P. Massaro 2021 Irrevocable Trust, of which the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16 or for any other purpose, except to the extent of the Reporting Person's pecuniary interests therein, if any.
Signature
/s/ Michael Massaro|2026-02-26