Massaro Michael, CEO of Flywire Corp (FLYW), made one open market sale of common shares in the last year, totaling $1.85 million. His most recent sale occurred on March 2, 2026. These sales rank 3,654th among 11,678 insiders in our database, where the average is $8.6 million across about 6.4 transactions per insider. He reported no open market purchases during this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| March 16, 2026 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 14087 | $3.95 | 3,315,776.0000 | 127,675,613 | 0.43% | 0.01% |
| March 16, 2026 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 14087 | $0.00 | 544,326.0000 | 127,675,613 | 2.52% | 0.01% |
| March 2, 2026 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 105021 | $12.43 | 3,301,689.0000 | 127,675,613 | 3.08% | 0.08% |
| March 2, 2026 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 150000 | $12.31 | 3,406,710.0000 | 127,675,613 | 4.22% | 0.12% |
| Dec. 24, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | G | Voting Common Stock | 465043 | $0.00 | 2,804,899.0000 | 127,675,613 | 19.87% | 0.36% |
| Feb. 24, 2026 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | A | Voting Common Stock | 751811 | $0.00 | 3,556,710.0000 | 127,675,613 | 26.80% | 0.59% |
| Dec. 24, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | G | Voting Common Stock | 465043 | $0.00 | 3,556,710.0000 | 127,675,613 | 11.56% | 0.36% |
| Dec. 1, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 26514 | $13.78 | 2,803,656.0000 | 127,675,613 | 0.94% | 0.02% |
| Sept. 2, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 26514 | $13.13 | 2,830,170.0000 | 129,339,462 | 0.93% | 0.02% |
| June 2, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 26514 | $10.79 | 2,856,684.0000 | 129,339,462 | 0.92% | 0.02% |
| March 13, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | A | Voting Common Stock | 765550 | $0.00 | 2,883,198.0000 | 129,339,462 | 36.15% | 0.59% |
| March 3, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 54145 | $10.76 | 2,117,648.0000 | 129,339,462 | 2.49% | 0.04% |
| Feb. 28, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 41587 | $0.00 | 558,413.0000 | 129,339,462 | 6.93% | 0.03% |
| Feb. 28, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 18435 | $0.00 | 0.0000 | 129,339,462 | 100.00% | 0.01% |
| Feb. 28, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 88731 | $0.00 | 0.0000 | 129,339,462 | 100.00% | 0.07% |
| Feb. 28, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 41587 | $3.95 | 2,171,793.0000 | 129,339,462 | 1.95% | 0.03% |
| Feb. 28, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 18435 | $3.28 | 2,130,206.0000 | 129,339,462 | 0.87% | 0.01% |
| Feb. 28, 2025 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 88731 | $0.59 | 2,111,771.0000 | 129,339,462 | 4.39% | 0.07% |
| Dec. 23, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | G | Voting Common Stock | 657236 | $0.00 | 2,023,040.0000 | 129,321,537 | 24.52% | 0.51% |
| Dec. 23, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | G | Voting Common Stock | 657236 | $0.00 | 2,023,040.0000 | 129,321,537 | 48.12% | 0.51% |
| Dec. 2, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 16213 | $23.14 | 2,023,040.0000 | 129,321,537 | 0.80% | 0.01% |
| Sept. 5, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 7646 | $17.31 | 2,039,253.0000 | 114,828,494 | 0.37% | 0.01% |
| Sept. 3, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 8629 | $18.04 | 2,046,899.0000 | 114,828,494 | 0.42% | 0.01% |
| June 5, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 7631 | $16.69 | 2,054,430.0000 | 114,828,494 | 0.37% | 0.01% |
| June 3, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 8698 | $16.95 | 2,062,061.0000 | 114,828,494 | 0.42% | 0.01% |
| May 3, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 107538 | $0.35 | 2,070,759.0000 | 114,828,494 | 5.48% | 0.09% |
| May 3, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 107538 | $0.00 | 0.0000 | 114,828,494 | 100.00% | 0.09% |
| April 3, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4892 | $24.07 | 1,963,221.0000 | 114,828,494 | 0.25% | 0.00% |
| April 3, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 13043 | $24.07 | 1,963,221.0000 | 114,828,494 | 0.66% | 0.01% |
| March 20, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 6311 | $25.06 | 1,981,156.0000 | 114,828,494 | 0.32% | 0.01% |
| March 20, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 16828 | $25.06 | 1,981,156.0000 | 114,828,494 | 0.84% | 0.01% |
| March 19, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 18689 | $25.11 | 1,987,467.0000 | 114,828,494 | 0.93% | 0.02% |
| March 19, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 49844 | $25.11 | 1,997,984.0000 | 114,828,494 | 2.43% | 0.04% |
| March 5, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 7644 | $27.18 | 2,072,828.0000 | 114,828,494 | 0.37% | 0.01% |
| March 4, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 28822 | $27.30 | 2,080,472.0000 | 114,828,494 | 1.37% | 0.03% |
| March 2, 2024 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | A | Voting Common Stock | 340867 | $0.00 | 2,109,294.0000 | 114,828,494 | 19.28% | 0.30% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 411464 | $23.29 | 1,768,427.0000 | 107,935,514 | 18.88% | 0.38% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 93938 | $0.00 | 0.0000 | 107,935,514 | 100.00% | 0.09% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 40815 | $0.00 | 88,731.0000 | 107,935,514 | 31.51% | 0.04% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 78983 | $0.00 | 107,538.0000 | 107,935,514 | 42.35% | 0.07% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Employee Stock Option (right to buy) | 739821 | $0.00 | 18,435.0000 | 107,935,514 | 97.57% | 0.69% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 739821 | $3.28 | 2,179,891.0000 | 107,935,514 | 51.37% | 0.69% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 38808 | $23.28 | 1,440,070.0000 | 107,935,514 | 2.62% | 0.04% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 78983 | $0.35 | 1,478,878.0000 | 107,935,514 | 5.64% | 0.07% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | F | Voting Common Stock | 20268 | $23.33 | 1,399,895.0000 | 107,935,514 | 1.43% | 0.02% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 40815 | $0.59 | 1,420,163.0000 | 107,935,514 | 2.96% | 0.04% |
| Dec. 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 93938 | $0.20 | 1,379,348.0000 | 107,935,514 | 7.31% | 0.09% |
| Dec. 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 7679 | $23.40 | 1,285,410.0000 | 107,935,514 | 0.59% | 0.01% |
| Oct. 17, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.00 | 1,303,838.0000 | 107,935,514 | 0.87% | 0.01% |
| Oct. 18, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 10749 | $29.03 | 1,293,089.0000 | 107,935,514 | 0.82% | 0.01% |
| Oct. 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.76 | 1,315,295.0000 | 107,935,514 | 0.86% | 0.01% |
| Oct. 4, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 10857 | $29.38 | 1,327,352.0000 | 107,935,514 | 0.81% | 0.01% |
| Oct. 4, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 600 | $30.30 | 1,326,752.0000 | 107,935,514 | 0.05% | 0.00% |
| Sept. 19, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.20 | 1,338,209.0000 | 107,935,514 | 0.85% | 0.01% |
| Sept. 18, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.93 | 1,349,666.0000 | 107,935,514 | 0.84% | 0.01% |
| Sept. 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 7742 | $33.75 | 1,384,037.0000 | 107,935,514 | 0.56% | 0.01% |
| Sept. 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $33.82 | 1,372,580.0000 | 107,935,514 | 0.83% | 0.01% |
| Sept. 6, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $33.40 | 1,361,123.0000 | 107,935,514 | 0.83% | 0.01% |
| Aug. 29, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $31.95 | 1,403,236.0000 | 107,935,514 | 0.81% | 0.01% |
| Aug. 30, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $32.99 | 1,391,779.0000 | 107,935,514 | 0.82% | 0.01% |
| Aug. 17, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.70 | 1,426,150.0000 | 107,935,514 | 0.80% | 0.01% |
| Aug. 18, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.27 | 1,414,693.0000 | 107,935,514 | 0.80% | 0.01% |
| Aug. 1, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Voting Common Stock | 35750 | $3.28 | 1,437,607.0000 | 107,935,514 | 2.55% | 0.03% |
| Aug. 1, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | M | Stock Option (right to buy) | 35750 | $0.00 | 758,258.0000 | 107,935,514 | 4.50% | 0.03% |
| July 12, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.84 | 1,412,270.0000 | 107,935,514 | 0.80% | 0.01% |
| July 13, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.96 | 1,400,813.0000 | 107,935,514 | 0.81% | 0.01% |
| June 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 7622 | $31.30 | 1,423,727.0000 | 107,935,514 | 0.53% | 0.01% |
| July 3, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.92 | 1,442,806.0000 | 107,935,514 | 0.79% | 0.01% |
| July 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.93 | 1,431,349.0000 | 107,935,514 | 0.79% | 0.01% |
| June 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $31.26 | 1,454,263.0000 | 107,935,514 | 0.78% | 0.01% |
| June 13, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $32.31 | 1,465,720.0000 | 107,935,514 | 0.78% | 0.01% |
| June 6, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $31.18 | 1,477,177.0000 | 107,935,514 | 0.77% | 0.01% |
| June 5, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $31.04 | 1,488,634.0000 | 107,935,514 | 0.76% | 0.01% |
| May 30, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.66 | 1,511,548.0000 | 107,935,514 | 0.75% | 0.01% |
| May 31, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.30 | 1,500,091.0000 | 107,935,514 | 0.76% | 0.01% |
| May 16, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $30.54 | 1,534,462.0000 | 107,935,514 | 0.74% | 0.01% |
| May 17, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $28.85 | 1,523,005.0000 | 107,935,514 | 0.75% | 0.01% |
| April 12, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 11457 | $29.27 | 1,545,919.0000 | 107,935,514 | 0.74% | 0.01% |
| April 11, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 25740 | $28.70 | 1,557,426.0000 | 107,935,514 | 1.63% | 0.02% |
| April 11, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 50 | $29.27 | 1,557,376.0000 | 107,935,514 | 0.00% | 0.00% |
| April 4, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 19033 | $29.11 | 1,583,166.0000 | 107,935,514 | 1.19% | 0.02% |
| April 3, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 27138 | $29.11 | 1,602,199.0000 | 107,935,514 | 1.67% | 0.03% |
| March 28, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 24296 | $27.31 | 1,639,669.0000 | 107,935,514 | 1.46% | 0.02% |
| March 29, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 8332 | $27.99 | 1,631,337.0000 | 107,935,514 | 0.51% | 0.01% |
| March 29, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 2000 | $29.04 | 1,629,337.0000 | 107,935,514 | 0.12% | 0.00% |
| March 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | A | Voting Common Stock | 284436 | $0.00 | 1,690,844.0000 | 107,935,514 | 20.22% | 0.26% |
| March 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4166 | $25.80 | 1,686,678.0000 | 107,935,514 | 0.25% | 0.00% |
| March 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 700 | $27.00 | 1,685,978.0000 | 107,935,514 | 0.04% | 0.00% |
| March 14, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 22013 | $26.31 | 1,663,965.0000 | 107,935,514 | 1.31% | 0.02% |
| March 13, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4166 | $24.04 | 1,406,408.0000 | 107,935,514 | 0.30% | 0.00% |
| Feb. 13, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4166 | $26.31 | 1,410,574.0000 | 107,935,514 | 0.29% | 0.00% |
| Feb. 10, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4666 | $26.11 | 1,414,740.0000 | 107,935,514 | 0.33% | 0.00% |
| Feb. 2, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 49202 | $28.76 | 1,430,138.0000 | 107,935,514 | 3.33% | 0.05% |
| Feb. 3, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 10732 | $28.56 | 1,419,406.0000 | 107,935,514 | 0.75% | 0.01% |
| Jan. 12, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4166 | $25.60 | 1,479,340.0000 | 107,935,514 | 0.28% | 0.00% |
| Jan. 11, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4166 | $25.20 | 1,483,506.0000 | 107,935,514 | 0.28% | 0.00% |
| Jan. 4, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 4166 | $24.44 | 1,487,672.0000 | 107,935,514 | 0.28% | 0.00% |
| Jan. 3, 2023 | Flywire Corp | $FLYW | Massaro Michael | Chief Executive Officer | S | Voting Common Stock | 20862 | $24.43 | 1,491,838.0000 | 107,935,514 | 1.38% | 0.02% |