Massaro Michael 4
4 · Flywire Corp · Filed Jul 20, 2026
Research Summary
AI-generated summary of this filing
Flywire (FLYW) CEO Michael Massaro Sells 125,000 Shares
What Happened
Michael Massaro, CEO of Flywire Corp (FLYW), sold a total of 125,000 shares in two open-market transactions executed under a previously adopted Rule 10b5-1 trading plan. On July 16, 2026 he sold 92,672 shares at a weighted-average price of $18.62 for proceeds of $1,725,729 (shares sold across prices from $18.48 to $18.915). On July 17, 2026 he sold 32,328 shares at a weighted-average price of $18.20 for proceeds of $588,295 (shares sold across prices from $18.06 to $18.585). Total proceeds were approximately $2,314,024. These were sales (not purchases), often routine when done under pre-set plans.
Key Details
- Transaction dates and prices:
- 2026-07-16: 92,672 shares sold, weighted avg $18.62; per filing prices ranged $18.48–$18.915 (Footnote F2).
- 2026-07-17: 32,328 shares sold, weighted avg $18.20; per filing prices ranged $18.06–$18.585 (Footnote F3).
- Total shares sold: 125,000; total proceeds ≈ $2,314,024.
- Plan: Sales were made pursuant to a previously adopted Rule 10b5-1 trading plan (Footnote F1).
- Trust holdings: Some shares reported in the filing are held in trusts (M Massaro Trust and Michael P. Massaro 2021 Irrevocable Trust); Massaro disclaims beneficial ownership of those trust-held shares (Footnotes F4 & F5).
- Filing timeliness: Form 4 was filed on 2026-07-20 for transactions dated 2026-07-16 and 07-17 — filed within the required two-business-day window (not late).
- Shares owned after transaction: Not disclosed in the provided excerpt.
Context
- Sales under 10b5-1 plans are pre-arranged and legally permit insiders to sell shares on a set schedule; they are commonly viewed as routine or for diversification/liquidity rather than a direct signal of sentiment.
- No options, awards, gifts, or tax-withholding events are reported in the provided transactions.
Insider Transaction Report
Form 4
Flywire CorpFLYW
Massaro Michael
DirectorChief Executive Officer
Transactions
- Sale
Voting Common Stock
[F1][F2]2026-07-16$18.62/sh−92,672$1,725,729→ 2,585,379 total - Sale
Voting Common Stock
[F1][F3]2026-07-17$18.20/sh−32,328$588,295→ 2,553,051 total
Holdings
- 192,193(indirect: See footnote)
Voting Common Stock
[F4] - 307,548(indirect: See footnote)
Voting Common Stock
[F5]
Footnotes (5)
- [F1]Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan.
- [F2]The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $18.48 to $18.915, inclusive. The Reporting Person has provided to the Issuer, and undertakes to provide to the staff of the Securities and Exchange Commission or any security holder of the Issuer, upon request, full information regarding the number of shares sold at each separate price within the range.
- [F3]The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $18.06 to $18.585, inclusive. The Reporting Person has provided to the Issuer, and undertakes to provide to the staff of the Securities and Exchange Commission or any security holder of the Issuer, upon request, full information regarding the number of shares sold at each separate price within the range.
- [F4]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.
- [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|2026-07-20