Michael Massaro insider trades: Flywire (FLYW) stock sales
Trades on the price chart
Daily close, with an arrow on each day they bought or sold
Companies
Where Michael reports to the SEC
Open-market buys and sales
52 trades reported on SEC Form 4, newest first
| Date | Stock | Type | Shares | Price | Value | Holding | Reported |
|---|---|---|---|---|---|---|---|
| Sep 1, 2026 | FLYW | ↓ Sell | 112,500 | $18.39 | $2.1M | Direct | Sep 3, 2026 (2d) |
| Jul 17, 2026 | FLYW | ↓ Sell | 125,000 | $18.51 | $2.3M | Direct | Jul 20, 2026 (3d) |
| Jun 15, 2026 | FLYW | ↓ Sell | 50,000 | $15.26 | $763K | Direct | Jun 17, 2026 (2d) |
| May 6, 2026 | FLYW | ↓ Sell | 50,000 | $16.39 | $820K | Direct | May 8, 2026 (2d) |
| Mar 2, 2026 | FLYW | ↓ Sell | 150,000 | $12.31 | $1.8M | Direct | Mar 4, 2026 (2d) |
| Sep 5, 2024 | FLYW | ↓ Sell | 7,646 | $17.31 | $132K | Direct | Sep 9, 2024 (4d) |
| Sep 3, 2024 | FLYW | ↓ Sell | 8,629 | $18.04 | $156K | Direct | Sep 5, 2024 (2d) |
| Jun 5, 2024 | FLYW | ↓ Sell | 7,631 | $16.69 | $127K | Direct | Jun 7, 2024 (2d) |
| Jun 3, 2024 | FLYW | ↓ Sell | 8,698 | $16.95 | $147K | Direct | Jun 5, 2024 (2d) |
| Apr 3, 2024 | FLYW | ↓ Sell | 13,043 | $24.07 | $314K | Direct | Apr 5, 2024 (2d) |
| Apr 3, 2024 | FLYW | ↓ Sell | 4,892 | $24.07 | $118K | Indirect | Apr 5, 2024 (2d) |
| Mar 20, 2024 | FLYW | ↓ Sell | 66,672 | $25.10 | $1.7M | Direct | Mar 21, 2024 (1d) |
| Mar 20, 2024 | FLYW | ↓ Sell | 25,000 | $25.10 | $628K | Indirect | Mar 21, 2024 (1d) |
| Mar 5, 2024 | FLYW | ↓ Sell | 36,466 | $27.27 | $995K | Direct | Mar 6, 2024 (1d) |
| Dec 5, 2023 | FLYW | ↓ Sell | 7,679 | $23.40 | $180K | Direct | Dec 7, 2023 (2d) |
| Oct 18, 2023 | FLYW | ↓ Sell10b5-1 | 22,206 | $29.01 | $644K | Direct | Oct 19, 2023 (1d) |
| Oct 5, 2023 | FLYW | ↓ Sell10b5-1 | 22,914 | $29.59 | $678K | Direct | Oct 6, 2023 (1d) |
| Sep 19, 2023 | FLYW | ↓ Sell10b5-1 | 22,914 | $30.56 | $700K | Direct | Sep 20, 2023 (1d) |
| Sep 6, 2023 | FLYW | ↓ Sell10b5-1 | 30,656 | $33.65 | $1.0M | Direct | Sep 7, 2023 (1d) |
| Aug 30, 2023 | FLYW | ↓ Sell10b5-1 | 22,914 | $32.47 | $744K | Direct | Aug 31, 2023 (1d) |
| Aug 18, 2023 | FLYW | ↓ Sell10b5-1 | 22,914 | $30.49 | $699K | Direct | Aug 21, 2023 (3d) |
| Jul 13, 2023 | FLYW | ↓ Sell | 22,914 | $30.40 | $697K | Direct | Jul 14, 2023 (1d) |
| Jul 5, 2023 | FLYW | ↓ Sell | 22,914 | $30.43 | $697K | Direct | Jul 6, 2023 (1d) |
| Jun 14, 2023 | FLYW | ↓ Sell | 22,914 | $31.79 | $728K | Direct | Jun 15, 2023 (1d) |
| Jun 6, 2023 | FLYW | ↓ Sell | 22,914 | $31.11 | $713K | Direct | Jun 7, 2023 (1d) |
| Jun 5, 2023 | FLYW | ↓ Sell | 7,622 | $31.30 | $239K | Direct | Jul 7, 2023 (32d) |
| May 31, 2023 | FLYW | ↓ Sell | 22,914 | $29.48 | $676K | Direct | Jun 1, 2023 (1d) |
| May 17, 2023 | FLYW | ↓ Sell | 22,914 | $29.70 | $680K | Direct | May 18, 2023 (1d) |
| Apr 12, 2023 | FLYW | ↓ Sell | 37,247 | $28.87 | $1.1M | Direct | Apr 13, 2023 (1d) |
| Apr 4, 2023 | FLYW | ↓ Sell | 46,171 | $29.11 | $1.3M | Direct | Apr 5, 2023 (1d) |
| Mar 29, 2023 | FLYW | ↓ Sell | 34,628 | $27.57 | $955K | Direct | Mar 30, 2023 (1d) |
| Mar 14, 2023 | FLYW | ↓ Sell | 31,045 | $25.95 | $806K | Direct | Mar 15, 2023 (1d) |
| Feb 13, 2023 | FLYW | ↓ Sell | 8,832 | $26.20 | $231K | Direct | Feb 14, 2023 (1d) |
| Feb 3, 2023 | FLYW | ↓ Sell | 59,934 | $28.73 | $1.7M | Direct | Feb 6, 2023 (3d) |
| Jan 12, 2023 | FLYW | ↓ Sell | 8,332 | $25.40 | $212K | Direct | Jan 13, 2023 (1d) |
| Jan 4, 2023 | FLYW | ↓ Sell | 25,028 | $24.43 | $611K | Direct | Jan 5, 2023 (1d) |
| Oct 4, 2022 | FLYW | ↓ Sell | 9,660 | $24.80 | $240K | Direct | Oct 5, 2022 (1d) |
| Sep 21, 2022 | FLYW | ↓ Sell | 9,660 | $24.33 | $235K | Direct | Sep 22, 2022 (1d) |
| Sep 8, 2022 | FLYW | ↓ Sell | 9,660 | $25.12 | $243K | Direct | Sep 9, 2022 (1d) |
| Aug 30, 2022 | FLYW | ↓ Sell | 9,660 | $25.01 | $242K | Direct | Aug 31, 2022 (1d) |
| Aug 17, 2022 | FLYW | ↓ Sell | 116,500 | $27.91 | $3.3M | Direct | Aug 18, 2022 (1d) |
| Apr 28, 2022 | FLYW | ↓ Sell | 31,089 | $30.85 | $959K | Direct | Apr 29, 2022 (1d) |
| Apr 12, 2022 | FLYW | ↓ Sell | 50,014 | $29.23 | $1.5M | Direct | Apr 13, 2022 (1d) |
| Mar 14, 2022 | FLYW | ↓ Sell | 600 | $24.28 | $15K | Direct | Mar 16, 2022 (2d) |
| Mar 3, 2022 | FLYW | ↓ Sell | 9,660 | $26.05 | $252K | Direct | Mar 4, 2022 (1d) |
| Feb 24, 2022 | FLYW | ↓ Sell | 9,660 | $25.53 | $247K | Direct | Feb 25, 2022 (1d) |
| Feb 18, 2022 | FLYW | ↓ Sell | 15,018 | $27.24 | $409K | Direct | Feb 23, 2022 (5d) |
| Jan 25, 2022 | FLYW | ↓ Sell | 10,260 | $26.63 | $273K | Direct | Jan 26, 2022 (1d) |
| Jan 6, 2022 | FLYW | ↓ Sell | 24,160 | $33.38 | $806K | Direct | Jan 7, 2022 (1d) |
| Dec 21, 2021 | FLYW | ↓ Sell | 24,200 | $33.86 | $819K | Direct | Dec 22, 2021 (1d) |
Each row is one filing's trades in one stock, summed. Shares and prices are as filed, before any later stock split.
Other FLYW insiders
Open-market trades in the last 12 months
About Michael Massaro's insider trades
Michael Massaro is Chief Executive Officer at Flywire (FLYW). Since Nov 30, 2021, Michael has reported no open-market purchases and 52 sales worth $39.3M on SEC Form 4. In the last 12 months: 5 sales ($7.8M).
6 sales (11% of the value sold) were made under a Rule 10b5-1 trading plan, which is set up months in advance and runs on a schedule, so they say little about how the insider sees the stock today.
Their filings also include shares withheld for taxes (10 filings), option exercises (7 filings), grants and awards (5 filings), gifts (5 filings). These aren't open-market trades and aren't counted above.
How to read insider trades
Officers, directors and owners of more than 10% of a company must report trades in its stock on SEC Form 4, usually within two business days. Purchases with their own money are the stronger signal: insiders sell for many reasons (taxes, diversification, a house), but buy for one. See every FLYW insider trade, the latest insider trades across the market, or cluster buys, when several insiders buy the same stock within days.