Flywire CEO sells 50,000 shares under 10b5-1 plan
Flywire Corp Chief Executive Officer Michael Massaro reported an open-market sale of 50,000 shares of Voting Common Stock on June 15, 2026.
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Form Type
4
Rhea-AI Filing Summary
Flywire Corp Chief Executive Officer Michael Massaro reported an open-market sale of 50,000 shares of Voting Common Stock on June 15, 2026. The shares were sold at a weighted average price of $15.2588 per share under a previously adopted Rule 10b5-1 trading plan.
After this transaction, Massaro directly holds 2,678,051 shares of Voting Common Stock. Additional shares are held indirectly through the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust, where his spouse serves as trustee and he disclaims beneficial ownership except for any pecuniary interests.
Insider Trade Summary 10b5-1
Net Seller: 50,000 shares
Net Sell
3 txns
Insider
Massaro Michael
Role
Chief Executive Officer
Sold
50,000 shs ($763K)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Sale | Voting Common Stock | 50,000 | $15.2588 | $763K |
| holding | Voting Common Stock | -- | -- | -- |
| holding | Voting Common Stock | -- | -- | -- |
Holdings After Transaction:
Voting Common Stock — 2,678,051 shares (Direct);
Voting Common Stock — 499,741 shares (Indirect, See footnote)
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 $15.01 to $15.49, 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. Adjusted to reflect 1,815 shares acquired under the Issuer's Employee Stock Purchase Plan.
- 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 sold: 50,000 shares
Weighted average sale price: $15.2588 per share
Direct holdings after sale: 2,678,051 shares
+3 more
6 metrics
Shares sold
50,000 shares
Open-market sale of Voting Common Stock on June 15, 2026
Weighted average sale price
$15.2588 per share
Sale prices ranged from $15.01 to $15.49
Direct holdings after sale
2,678,051 shares
Voting Common Stock held directly by CEO after transaction
Indirect trust holding (M Massaro Trust)
307,548 shares
Held by M Massaro Trust; CEO disclaims beneficial ownership except pecuniary interests
Indirect trust holding (2021 Irrevocable Trust)
192,193 shares
Held by Michael P. Massaro 2021 Irrevocable Trust; CEO disclaims beneficial ownership except pecuniary interests
ESPP acquisition adjustment
1,815 shares
Acquired under Flywire’s Employee Stock Purchase Plan and reflected in holdings
Key Terms
Rule 10b5-1 trading plan, weighted average price, Employee Stock Purchase Plan, pecuniary interests, +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.
Employee Stock Purchase Plan financial
"Adjusted to reflect 1,815 shares acquired under the Issuer's Employee Stock Purchase Plan."
An employee stock purchase plan is a company program that lets workers buy shares through small payroll deductions, often at a discount to the market price and after a set offering period. Think of it like a workplace savings plan that turns into ownership: it encourages employees to share in the company’s success and can create predictable buying or selling of stock that investors watch because it affects supply, demand and employee incentives.
pecuniary interests financial
"except to the extent of the Reporting Person's pecuniary interests therein, if any."
disclaims beneficial ownership regulatory
"The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What insider transaction did Flywire (FLYW) CEO Michael Massaro report?
Michael Massaro reported selling 50,000 shares of Flywire Voting Common Stock. The sale occurred on June 15, 2026, as an open-market transaction executed under a previously adopted Rule 10b5-1 trading plan, indicating it was pre-scheduled rather than a discretionary trade.
What indirect Flywire (FLYW) holdings are reported for Michael Massaro?
The filing shows indirect holdings through the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust. Both are overseen by his spouse as trustee, and Massaro disclaims beneficial ownership except for any pecuniary interests in those trust-held shares.
How is the Flywire (FLYW) CEO’s sale characterized in the Form 4?
The sale is coded as an open-market or private sale of non-derivative Voting Common Stock. There are no derivative exercises reported, and the transaction is presented alongside updated direct and indirect share balances, giving a snapshot of the CEO’s overall equity position.
AI-generated analysis. How Rhea-AI works. Not financial advice.
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