Form 4: Flywire CEO Exercises Stock Options Under 10b5-1 Plan

Flywire Corp CEO Michael Massaro acquired 14,087 shares of common stock through an option exercise at $3.95 per share.

Summary

• Michael Massaro, Flywire Corp's Chief Executive Officer and Director, acquired 14,087 shares of Voting Common Stock.
• The transaction occurred on March 16, 2026, through the exercise of employee stock options at a price of $3.95 per share.
• The acquisition was made pursuant to a Rule 10b5-1(c) plan, indicating a pre-arranged transaction.
• Following this transaction, Mr. Massaro directly beneficially owns 2,816,035 shares of Voting Common Stock.
• He also indirectly beneficially owns 192,193 shares through the M Massaro Trust and 307,548 shares through the Michael P. Massaro 2021 Irrevocable Trust, for which he disclaims beneficial ownership.
• After the exercise, 544,326 employee stock options remain, with an exercise price of $3.95 and an expiration date of January 20, 2031.

Sentiment

Score: 6

Explanation: StockSavvy.ai views this as a neutral to slightly positive event. It's a routine insider transaction, pre-planned under a 10b5-1 plan, and the acquisition of shares by a CEO is generally not a negative signal.

Positives

• The exercise of employee stock options at a fixed price of $3.95 is financially beneficial for the reporting person, Michael Massaro.
• The transaction was conducted under a Rule 10b5-1(c) plan, indicating a pre-scheduled and orderly insider transaction.

Future Outlook

This Form 4 filing does not contain any forward-looking statements or guidance regarding the company's future performance.

Industry Context

StockSavvy.ai notes that insider option exercises, especially those conducted under a Rule 10b5-1 plan, are routine transactions for executives. While not a direct signal of future company performance, they reflect personal financial planning and the monetization of vested equity compensation.

Related Party Transactions

• Shares are held by the M Massaro Trust, where the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership.
• Shares are held by the Michael P. Massaro 2021 Irrevocable Trust, where the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership.

Stakeholder Impact

• Shareholders: Minimal impact as this is a routine, pre-planned insider transaction involving a relatively small number of shares compared to the company's total outstanding shares.

Key Dates

Keywords

Flywire, FLYW, Michael Massaro, Stock Option Exercise, Insider Transaction, SEC Form 4, Common Stock, CEO, 10b5-1 Plan