InsiderTrades

Massaro Michael

SEC CIK 1862130 · EDGAR

Buying vs selling by month open-market trades, last 59 months, FLYW
BoughtSold

Companies

TickerCompanyTitleHoldingBoughtSoldTradesFirstLast
FLYWFlywire CorpCEO, Dir 2.51M — $38.62M 832021-10-292026-09-01

Most active insiders at FLYW, 12 months

#InsiderTitleBoughtSold
1 Voss Capital, LP10% —$10.34M
2 Massaro MichaelCEO, Dir —$7.81M
3 Voss Value Master Fund, LP10% $3.48M—
4 Orgel RobPres, COO —$3.04M
5 Riese Phillip JohnDir —$1.63M
6 Butterfield PeterGC, CCO —$1.44M
7 Kansal MohitChief Payments Off —$1.38M
8 Pitigoi CosminCFO —$1.03M
9 King David R.See Remarks —$659.7K
10 Santos Edwin JDir —$245.8K

Transactions 83

Type
Reset
X Filed Traded Ticker Company Insider Title Type Price Qty Owned ΔOwn Value
T 2026-09-03 16:05 2026-09-01 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $18.18 -40.0K 2.51M -2% -$727.3K
T 2026-09-03 16:05 2026-09-01 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $18.39 -112.5K 2.40M -4% -$2.07M
MT 2026-07-20 16:11 2026-07-16+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $18.51 -125.0K 2.55M -5% -$2.31M
T 2026-06-17 16:14 2026-06-15 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $15.26 -50.0K 2.68M -2% -$762.9K
2026-06-03 16:28 2026-06-01 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $16.61 -39.8K 2.73M -1% -$661.1K
MT 2026-05-08 16:27 2026-05-06 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $16.39 -50.0K 2.77M -2% -$819.7K
D 2026-03-18 2026-03-16 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $3.95 +14.1K 2.82M +0.5% +$55.6K
T 2026-03-04 2026-03-02 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $12.43 -105.0K 2.80M -4% -$1.31M
T 2026-03-04 2026-03-02 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $12.31 -150.0K 2.91M -5% -$1.85M
2026-02-26 2025-12-24 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 +465.0K 2.31M +25% $0
2026-02-26 2026-02-24 FLYW Flywire Corp Massaro Michael CEO, Dir A - Grant $0.00 +751.8K 3.06M +33% $0
I 2026-02-26 2025-12-24 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 -465.0K 192.2K -71% $0
2025-12-03 2025-12-01 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $13.78 -26.5K 1.84M -1% -$365.4K
2025-09-04 2025-09-02 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $13.13 -26.5K 1.87M -1% -$348.1K
2025-06-04 2025-06-02 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $10.79 -26.5K 1.89M -1% -$286.1K
2025-03-17 2025-03-13 FLYW Flywire Corp Massaro Michael CEO, Dir A - Grant $0.00 +765.5K 1.92M +66% $0
2025-03-05 2025-03-03 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $10.76 -54.1K 1.15M -4% -$582.6K
DM 2025-03-04 2025-02-28 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $1.86 +148.8K 1.15M +15% +$277.1K
2024-12-27 2024-12-23 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 -657.2K 1.06M -38% $0
I 2024-12-27 2024-12-23 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 +657.2K 657.2K New $0
2024-12-04 2024-12-02 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $23.14 -16.2K 1.72M -0.9% -$375.2K
2024-09-09 2024-09-05 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $17.31 -7,646 1.73M -0.4% -$132.4K
2024-09-05 2024-09-03 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $18.04 -8,629 1.74M -0.5% -$155.7K
2024-06-07 2024-06-05 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $16.69 -7,631 1.75M -0.4% -$127.4K
2024-06-05 2024-06-03 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $16.95 -8,698 1.75M -0.5% -$147.4K
D 2024-05-07 2024-05-03 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $0.35 +107.5K 1.76M +6% +$37.6K
TI 2024-04-05 2024-04-03 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $24.07 -4,892 307.5K -2% -$117.8K
T 2024-04-05 2024-04-03 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $24.07 -13.0K 1.66M -0.8% -$313.9K
MT 2024-03-21 2024-03-19+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.10 -66.7K 1.67M -4% -$1.67M
MTI 2024-03-21 2024-03-19+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.10 -25.0K 312.4K -7% -$627.4K
M 2024-03-06 2024-03-04+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $27.27 -36.5K 1.74M -2% -$994.6K
2024-03-05 2024-03-02 FLYW Flywire Corp Massaro Michael CEO, Dir A - Grant $0.00 +340.9K 1.77M +24% $0
DM 2023-12-15 2023-12-14 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $2.62 +953.6K 1.04M +1,079% +$2.50M
DM 2023-12-15 2023-12-14 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $23.29 -470.5K 1.06M -31% -$10.96M
2023-12-07 2023-12-05 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $23.40 -7,679 948.0K -0.8% -$179.7K
M 2023-10-19 2023-10-17+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $29.01 -22.2K 966.4K -2% -$644.3K
M 2023-10-06 2023-10-04+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $29.59 -22.9K 989.3K -2% -$678.1K
M 2023-09-20 2023-09-18+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $30.56 -22.9K 1.01M -2% -$700.4K
M 2023-09-07 2023-09-05+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $33.65 -30.7K 1.05M -3% -$1.03M
M 2023-08-31 2023-08-29+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $32.47 -22.9K 1.05M -2% -$744.0K
M 2023-08-21 2023-08-17+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $30.49 -22.9K 1.09M -2% -$698.5K
D 2023-08-03 2023-08-01 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $3.28 +35.8K 1.10M +3% +$117.3K
M 2023-07-14 2023-07-12+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $30.40 -22.9K 1.07M -2% -$696.6K
2023-07-07 2023-06-05 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $31.30 -7,622 1.09M -0.7% -$238.6K
M 2023-07-06 2023-07-03+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $30.42 -22.9K 1.09M -2% -$697.2K
M 2023-06-15 2023-06-13+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $31.79 -22.9K 1.13M -2% -$728.3K
M 2023-06-07 2023-06-05+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $31.11 -22.9K 1.15M -2% -$712.9K
M 2023-06-01 2023-05-30+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $29.48 -22.9K 1.16M -2% -$675.5K
M 2023-05-18 2023-05-16+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $29.70 -22.9K 1.19M -2% -$680.4K
M 2023-04-13 2023-04-11+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $28.88 -37.2K 1.17M -3% -$1.08M
M 2023-04-05 2023-04-03+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $29.11 -46.2K 1.20M -4% -$1.34M
M 2023-03-30 2023-03-28+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $27.57 -34.6K 1.25M -3% -$954.8K
M 2023-03-15 2023-03-13+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.95 -31.0K 1.02M -3% -$805.7K
2023-03-15 2023-03-14 FLYW Flywire Corp Massaro Michael CEO, Dir A - Grant $0.00 +284.4K 1.31M +28% $0
M 2023-02-14 2023-02-10+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $26.20 -8,832 1.03M -0.8% -$231.4K
M 2023-02-06 2023-02-02+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $28.72 -59.9K 1.05M -5% -$1.72M
M 2023-01-13 2023-01-11+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.40 -8,332 1.10M -0.8% -$211.6K
M 2023-01-05 2023-01-03+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $24.43 -25.0K 1.10M -2% -$611.5K
D 2022-12-27 2022-12-19 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 -25.0K 1.12M -2% $0
D 2022-12-27 2022-12-22 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $3.28 +12.5K 1.13M +1% +$41.0K
M 2022-10-05 2022-10-03+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $24.80 -9,660 1.11M -0.9% -$239.6K
M 2022-09-22 2022-09-20+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $24.33 -9,660 1.11M -0.9% -$235.0K
M 2022-09-09 2022-09-07+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.12 -9,660 1.12M -0.9% -$242.6K
M 2022-08-31 2022-08-29+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.01 -9,660 1.14M -0.8% -$241.6K
M 2022-08-18 2022-08-16+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $27.91 -116.5K 1.15M -9% -$3.25M
DMA 2022-06-03 2022-05-27 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $1.11 +260.0K 1.10M +31% +$287.9K
DMA 2022-06-03 2022-05-27 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $20.00 -104.8K 1.15M -8% -$2.10M
DM 2022-06-01 2022-05-27 FLYW Flywire Corp Massaro Michael CEO, Dir F - Tax $20.10 -104.7K 1.26M -8% -$2.10M
DM 2022-06-01 2022-05-27 FLYW Flywire Corp Massaro Michael CEO, Dir M - OptEx $1.11 +260.0K 1.36M +24% +$287.9K
M 2022-04-29 2022-04-27+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $30.85 -31.1K 1.12M -3% -$959.0K
M 2022-04-13 2022-04-11+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $29.23 -50.0K 1.14M -4% -$1.46M
2022-03-16 2022-03-14 FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $24.28 -600 1.19M -0.1% -$14.6K
2022-03-08 2022-03-04 FLYW Flywire Corp Massaro Michael CEO, Dir A - Grant $0.00 +252.0K 1.19M +27% $0
M 2022-03-04 2022-03-02+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $26.06 -9,660 934.1K -1% -$251.7K
M 2022-02-25 2022-02-23+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $25.52 -9,660 948.8K -1% -$246.6K
M 2022-02-23 2022-02-17+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $27.24 -15.0K 954.2K -2% -$409.1K
M 2022-01-26 2022-01-24+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $26.63 -10.3K 973.4K -1% -$273.2K
M 2022-01-07 2022-01-05+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $33.38 -24.2K 978.7K -2% -$806.3K
M 2021-12-22 2021-12-20+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $33.86 -24.2K 1.01M -2% -$819.4K
M 2021-12-09 2021-12-07+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $41.68 -24.2K 1.04M -2% -$1.01M
2021-12-09 2021-12-07 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 -30.0K 1.05M -3% $0
2021-12-01 2021-10-29 FLYW Flywire Corp Massaro Michael CEO, Dir G - Gift $0.00 -120.0K 1.11M -10% $0
ME 2021-12-01 2021-11-29+ FLYW Flywire Corp Massaro Michael CEO, Dir S - Sale $155,104.35 -24.2K 1.09M -2% —

Purchase Sale Sale after option exercise All abbreviations