Michael Massaro serves as Executive at Flywire Corp, where they oversee executive responsibilities. Since joining the company, Michael Massaro has executed 155 insider transactions totaling $31.4M, demonstrating a bearish approach to their equity position. Their most recent transaction on Dec 1, 2025 involved selling 26,514 shares valued at $365.4K.
Michael Massaro currently holds 1,838,872 shares of Flywire Corp (FLYW), valued at approximately $0. This represents their equity stake as Executive.
Based on SEC Form 4 filings, Michael Massaro has been a net seller of FLYW stock. They have purchased $0 and sold $31.4M worth of shares.
Michael Massaro's most recent insider trade was on Dec 1, 2025, when they sold 26,514 shares at $13.78 per share.
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| $13.13 |
| Discretionary |
| Sep 5, 2024 | FLYW | $132.4K | Sale | 7,646 | $17.31 | Discretionary |
| Sep 3, 2024 | FLYW | $155.7K | Sale | 8,629 | $18.04 | Discretionary |
| Jun 5, 2024 | FLYW | $127.4K | Sale | 7,631 | $16.69 | Discretionary |
| Jun 3, 2024 | FLYW | $147.4K | Sale | 8,698 | $16.95 | Discretionary |
| May 3, 2024 | FLYW | $37.6K | Option Exercise | 107,538 | $0.35 | Discretionary |
| Apr 3, 2024 | FLYW | $313.9K | Sale | 13,043 | $24.07 | Planned |
| Apr 3, 2024 | FLYW | $117.8K | Sale | 4,892 | $24.07 | Planned |
| Mar 20, 2024 | FLYW | $421.7K | Sale | 16,828 | $25.06 | Planned |
| Mar 20, 2024 | FLYW | $158.2K | Sale | 6,311 | $25.06 | Planned |
| Mar 19, 2024 | FLYW | $469.3K | Sale | 18,689 | $25.11 | Planned |
| Mar 19, 2024 | FLYW | $1.3M | Sale | 49,844 | $25.11 | Planned |
| Mar 5, 2024 | FLYW | $207.8K | Sale | 7,644 | $27.18 | Discretionary |
| Mar 4, 2024 | FLYW | $786.8K | Sale | 28,822 | $27.30 | Discretionary |
| Mar 2, 2024 | FLYW | $0 | Award | 340,867 | $N/A | Discretionary |
| Dec 14, 2023 | FLYW | $472.9K | Payment | 20,268 | $23.33 | Discretionary |
| Dec 14, 2023 | FLYW | $18.8K | Option Exercise | 93,938 | $0.20 | Discretionary |
| Dec 14, 2023 | FLYW | $27.6K | Option Exercise | 78,983 | $0.35 | Discretionary |
| Dec 14, 2023 | FLYW | $903.5K | Payment | 38,808 | $23.28 | Discretionary |
| Dec 14, 2023 | FLYW | $2.4M | Option Exercise | 739,821 | $3.28 | Discretionary |
| Dec 14, 2023 | FLYW | $9.6M | Payment | 411,464 | $23.29 | Discretionary |
| Dec 14, 2023 | FLYW | $24.1K | Option Exercise | 40,815 | $0.59 | Discretionary |
| Dec 5, 2023 | FLYW | $179.7K | Sale | 7,679 | $23.40 | Discretionary |
| Oct 18, 2023 | FLYW | $312.0K | Sale | 10,749 | $29.03 | Discretionary |
| Oct 17, 2023 | FLYW | $332.3K | Sale | 11,457 | $29.00 | Discretionary |
| Oct 5, 2023 | FLYW | $341.0K | Sale | 11,457 | $29.76 | Discretionary |
| Oct 4, 2023 | FLYW | $18.2K | Sale | 600 | $30.30 | Discretionary |
| Oct 4, 2023 | FLYW | $319.0K | Sale | 10,857 | $29.38 | Discretionary |
| Sep 19, 2023 | FLYW | $346.0K | Sale | 11,457 | $30.20 | Discretionary |