Michael Massaro

Companies

• FlywireBoard member May 25, 2021 to now¹
• FlywireChief executive officer May 25, 2021 to now¹

Holdings

Stock this person has reported owning, from the forms officers and directors file with the SEC. See the biggest insider stakes.

Shares held

• Flywire FLYW2,708,106 shares²$52.4M at $19.35Sep 3, 2026

As of each latest filing. The line shows shares held over time.

Recent filings

• Sep 1, 2026Sold 112,500 shares at $18.39 of Flywire²
• Sep 1, 2026Shares withheld for tax 39,993 shares at $18.19 of Flywire²
• Jul 17, 2026Sold 32,328 shares at $18.20 of Flywire³
• Jul 16, 2026Sold 92,672 shares at $18.62 of Flywire³
• Jun 15, 2026Sold 50,000 shares at $15.26 of Flywire⁴
• Jun 1, 2026Shares withheld for tax 39,799 shares at $16.61 of Flywire⁵
• May 6, 2026Sold 38,170 shares at $16.62 of Flywire⁶
• May 6, 2026Sold 11,830 shares at $15.65 of Flywire⁶
• Mar 16, 2026Exercised options 14,087 shares at $3.95 of Flywire⁷
• Mar 2, 2026Shares withheld for tax 105,021 shares at $12.43 of Flywire⁸
• Mar 2, 2026Sold 150,000 shares at $12.31 of Flywire⁸
• Feb 24, 2026Granted 751,811 shares of Flywire⁹
• Dec 24, 2025Gift 465,043 shares of Flywire⁹
• Dec 24, 2025Gift 465,043 shares of Flywire⁹
• Dec 1, 2025Shares withheld for tax 26,514 shares at $13.78 of Flywire¹⁰
• Sep 2, 2025Shares withheld for tax 26,514 shares at $13.13 of Flywire¹¹
• Jun 2, 2025Shares withheld for tax 26,514 shares at $10.79 of Flywire¹²
• Mar 13, 2025Granted 765,550 shares of Flywire¹³
• Mar 3, 2025Shares withheld for tax 54,145 shares at $10.76 of Flywire¹⁴
• Feb 28, 2025Exercised options 41,587 shares at $3.95 of Flywire¹⁵
• Feb 28, 2025Exercised options 18,435 shares at $3.28 of Flywire¹⁵
• Feb 28, 2025Exercised options 88,731 shares at $0.59 of Flywire¹⁵
• Dec 23, 2024Gift 657,236 shares of Flywire¹⁶
• Dec 23, 2024Gift 657,236 shares of Flywire¹⁶
• Dec 2, 2024Shares withheld for tax 16,213 shares at $23.14 of Flywire¹⁷