Flywire CEO sells 112,500 shares around $18
Flywire CEO Michael Massaro had shares withheld for taxes and sold additional shares under a Rule 10b5-1 trading plan.
Rhea-AI Filing Summary
Flywire Corp (FLYW) reported that Chief Executive Officer and director Michael Massaro disposed of Voting Common Stock on September 1, 2026. 39,993 shares were withheld at $18.185 per share to cover income tax obligations on net-settled restricted stock units, which was not an open-market sale, and 112,500 shares were sold at a weighted-average price of $18.3883 per share under a previously adopted Rule 10b5-1 trading plan. The filing also notes indirect holdings in family trusts for which Massaro disclaims beneficial ownership except for any pecuniary interest.
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Insights
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Insider Trade Summary 10b5-1
Net Seller: 112,500 shares
Net Sell
4 txns
Insider
Massaro Michael
Role
Chief Executive Officer
Sold
112,500 shs ($2.07M)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Tax Withholding | Voting Common Stock F1 | 39,993 | $18.185 | $727K |
| Sale | Voting Common Stock F2, F3 | 112,500 | $18.3883 | $2.07M |
| holding | Voting Common Stock F4 | -- | -- | -- |
| holding | Voting Common Stock F5 | -- | -- | -- |
Holdings After Transaction:
Voting Common Stock — 2,400,558 shares (Direct);
Voting Common Stock — 499,741 shares (Indirect, See footnote)
Footnotes (5)
- F1. Represents the number of shares of common stock that have been withheld by the Issuer to satisfy its income tax withholding and remittance obligations in connection with the net settlement of certain time-based restricted stock unit awards and does not represent an open market sale.
- F2. Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan.
- F3. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $18.11 to $18.77, 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.
Key Figures
Shares withheld for taxes: 39,993 shares
Tax withholding price: $18.185 per share
Shares sold: 112,500 shares
+1 more
4 metrics
Shares withheld for taxes
39,993 shares
Voting Common Stock withheld on September 1, 2026 to satisfy income tax obligations on RSUs
Tax withholding price
$18.185 per share
Price used for withholding 39,993 shares of Voting Common Stock
Shares sold
112,500 shares
Voting Common Stock sold on September 1, 2026
Weighted average sale price
$18.3883 per share
Weighted average price for 112,500 shares sold, with trades from $18.11 to $18.77
Key Terms
Rule 10b5-1 trading plan, weighted average price, net settlement, restricted stock unit, +1 more
5 terms
Rule 10b5-1 trading plan regulatory
"Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan"
A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.
weighted average price financial
"The price reported in Column 4 is a weighted average price"
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
net settlement financial
"in connection with the net settlement of certain time-based restricted stock unit awards"
restricted stock unit financial
"net settlement of certain time-based restricted stock unit awards"
A restricted stock unit is a promise from a company to give an employee shares of stock after certain conditions are met, like staying with the company for a set amount of time. It’s like earning a bonus that turns into company stock once you’ve proven your commitment, making it a way to motivate and reward employees.
pecuniary interests financial
"except to the extent of the Reporting Person's pecuniary interests therein"
FAQ
What insider transactions did FLYW CEO Michael Massaro report on September 1, 2026?
Michael Massaro reported two transactions in Flywire Corp (FLYW) Voting Common Stock on September 1, 2026: 39,993 shares withheld to satisfy income tax obligations on RSUs and an open-market or private sale of 112,500 shares at a weighted-average price of $18.3883 per share.
AI-generated analysis. How Rhea-AI works. Not financial advice.
