Follow the people · Insider
Michael Massaro
Michael Massaro files insider transactions with the SEC as a chief executive officer of Flywire (FLYW). We hold 6 disclosed purchases and sales filed since 28 May 2021, 4 of them in the last 90 days.
- Files forFLYW
- Disclosed buys and sells6 in all, 4 in the last 90 days
- Last disclosure3 September 2026
Positions held
1 post we hold — a term names its own dates; a run of filings only says when they filed- Filed 28 May 2021 — 1 September 2026Chief Executive Officer · Flywire (FLYW)204 Form 4 lines · source: SEC Form 4
Everything they disclosed
120 entries, newest first — one per disclosure report, one per Form 4 line- had shares withheld for tax on 39,993 shares of FlywireSEC Form 43 September 2026Voting Common Stock · traded 1 September 2026 · filed 3 September 2026
- ▼ sold on the open market 112,500 shares of FlywireSEC Form 43 September 2026Voting Common Stock · traded 1 September 2026 · filed 3 September 2026
- ▼ sold on the open market 92,672 shares of FlywireSEC Form 420 July 2026Voting Common Stock · traded 16 July 2026 · filed 20 July 2026
- ▼ sold on the open market 32,328 shares of FlywireSEC Form 420 July 2026Voting Common Stock · traded 17 July 2026 · filed 20 July 2026
- ▼ sold on the open market 50,000 shares of FlywireSEC Form 417 June 2026Voting Common Stock · traded 15 June 2026 · filed 17 June 2026
- had shares withheld for tax on 39,799 shares of FlywireSEC Form 43 June 2026Voting Common Stock · traded 1 June 2026 · filed 3 June 2026
- ▼ sold on the open market 11,830 shares of FlywireSEC Form 48 May 2026Voting Common Stock · traded 6 May 2026 · filed 8 May 2026
- ▼ sold on the open market 38,170 shares of FlywireSEC Form 48 May 2026Voting Common Stock · traded 6 May 2026 · filed 8 May 2026
- exercised options over 14,087 shares of FlywireSEC Form 418 March 2026Voting Common Stock · traded 16 March 2026 · filed 18 March 2026
- exercised options over 14,087 shares of Flywire (a derivative holding)SEC Form 418 March 2026Employee Stock Option (right to buy) · traded 16 March 2026 · filed 18 March 2026
- exercised options over 14,087 shares of Flywire (a derivative holding)SEC Form 418 March 2026Employee Stock Option (right to buy) · traded 16 March 2026 · filed 18 March 2026
- exercised options over 14,087 shares of FlywireSEC Form 418 March 2026Voting Common Stock · traded 16 March 2026 · filed 18 March 2026
- ▼ sold on the open market 150,000 shares of FlywireSEC Form 44 March 2026Voting Common Stock · traded 2 March 2026 · filed 4 March 2026
- had shares withheld for tax on 105,021 shares of FlywireSEC Form 44 March 2026Voting Common Stock · traded 2 March 2026 · filed 4 March 2026
- ▼ sold on the open market 150,000 shares of FlywireSEC Form 44 March 2026Voting Common Stock · traded 2 March 2026 · filed 4 March 2026
- had shares withheld for tax on 105,021 shares of FlywireSEC Form 44 March 2026Voting Common Stock · traded 2 March 2026 · filed 4 March 2026
- gave away 465,043 shares of FlywireSEC Form 426 February 2026Voting Common Stock · traded 24 December 2025 · filed 26 February 2026
- gave away 465,043 shares of FlywireSEC Form 426 February 2026Voting Common Stock · traded 24 December 2025 · filed 26 February 2026
- was granted 751,811 shares of FlywireSEC Form 426 February 2026Voting Common Stock · traded 24 February 2026 · filed 26 February 2026
- gave away 465,043 shares of FlywireSEC Form 426 February 2026Voting Common Stock · traded 24 December 2025 · filed 26 February 2026
- gave away 465,043 shares of FlywireSEC Form 426 February 2026Voting Common Stock · traded 24 December 2025 · filed 26 February 2026
- was granted 751,811 shares of FlywireSEC Form 426 February 2026Voting Common Stock · traded 24 February 2026 · filed 26 February 2026
- had shares withheld for tax on 26,514 shares of FlywireSEC Form 43 December 2025Voting Common Stock · traded 1 December 2025 · filed 3 December 2025
- had shares withheld for tax on 26,514 shares of FlywireSEC Form 44 September 2025Voting Common Stock · traded 2 September 2025 · filed 4 September 2025
- had shares withheld for tax on 26,514 shares of FlywireSEC Form 44 June 2025Voting Common Stock · traded 2 June 2025 · filed 4 June 2025
- was granted 765,550 shares of FlywireSEC Form 417 March 2025Voting Common Stock · traded 13 March 2025 · filed 17 March 2025
- had shares withheld for tax on 54,145 shares of FlywireSEC Form 45 March 2025Voting Common Stock · traded 3 March 2025 · filed 5 March 2025
- exercised options over 88,731 shares of Flywire (a derivative holding)SEC Form 44 March 2025Employee Stock Option (right to buy) · traded 28 February 2025 · filed 4 March 2025
- exercised options over 18,435 shares of Flywire (a derivative holding)SEC Form 44 March 2025Employee Stock Option (right to buy) · traded 28 February 2025 · filed 4 March 2025
- exercised options over 41,587 shares of Flywire (a derivative holding)SEC Form 44 March 2025Employee Stock Option (right to buy) · traded 28 February 2025 · filed 4 March 2025
- exercised options over 88,731 shares of FlywireSEC Form 44 March 2025Voting Common Stock · traded 28 February 2025 · filed 4 March 2025
- exercised options over 18,435 shares of FlywireSEC Form 44 March 2025Voting Common Stock · traded 28 February 2025 · filed 4 March 2025
- exercised options over 41,587 shares of FlywireSEC Form 44 March 2025Voting Common Stock · traded 28 February 2025 · filed 4 March 2025
- gave away 657,236 shares of FlywireSEC Form 427 December 2024Voting Common Stock · traded 23 December 2024 · filed 27 December 2024
- gave away 657,236 shares of FlywireSEC Form 427 December 2024Voting Common Stock · traded 23 December 2024 · filed 27 December 2024
- had shares withheld for tax on 16,213 shares of FlywireSEC Form 44 December 2024Voting Common Stock · traded 2 December 2024 · filed 4 December 2024
- ▼ sold on the open market 7,646 shares of FlywireSEC Form 49 September 2024Voting Common Stock · traded 5 September 2024 · filed 9 September 2024
- ▼ sold on the open market 8,629 shares of FlywireSEC Form 45 September 2024Voting Common Stock · traded 3 September 2024 · filed 5 September 2024
- ▼ sold on the open market 7,631 shares of FlywireSEC Form 47 June 2024Voting Common Stock · traded 5 June 2024 · filed 7 June 2024
- ▼ sold on the open market 8,698 shares of FlywireSEC Form 45 June 2024Voting Common Stock · traded 3 June 2024 · filed 5 June 2024
- exercised options over 107,538 shares of Flywire (a derivative holding)SEC Form 47 May 2024Employee Stock Option (right to buy) · traded 3 May 2024 · filed 7 May 2024
- exercised options over 107,538 shares of FlywireSEC Form 47 May 2024Voting Common Stock · traded 3 May 2024 · filed 7 May 2024
- ▼ sold on the open market 13,043 shares of FlywireSEC Form 45 April 2024Voting Common Stock · traded 3 April 2024 · filed 5 April 2024
- ▼ sold on the open market 4,892 shares of FlywireSEC Form 45 April 2024Voting Common Stock · traded 3 April 2024 · filed 5 April 2024
- ▼ sold on the open market 49,844 shares of FlywireSEC Form 421 March 2024Voting Common Stock · traded 19 March 2024 · filed 21 March 2024
- ▼ sold on the open market 18,689 shares of FlywireSEC Form 421 March 2024Voting Common Stock · traded 19 March 2024 · filed 21 March 2024
- ▼ sold on the open market 16,828 shares of FlywireSEC Form 421 March 2024Voting Common Stock · traded 20 March 2024 · filed 21 March 2024
- ▼ sold on the open market 6,311 shares of FlywireSEC Form 421 March 2024Voting Common Stock · traded 20 March 2024 · filed 21 March 2024
- ▼ sold on the open market 28,822 shares of FlywireSEC Form 46 March 2024Voting Common Stock · traded 4 March 2024 · filed 6 March 2024
- ▼ sold on the open market 7,644 shares of FlywireSEC Form 46 March 2024Voting Common Stock · traded 5 March 2024 · filed 6 March 2024
- was granted 340,867 shares of FlywireSEC Form 45 March 2024Voting Common Stock · traded 2 March 2024 · filed 5 March 2024
- exercised options over 93,938 shares of Flywire (a derivative holding)SEC Form 415 December 2023Employee Stock Option (right to buy) · traded 14 December 2023 · filed 15 December 2023
- exercised options over 40,815 shares of Flywire (a derivative holding)SEC Form 415 December 2023Employee Stock Option (right to buy) · traded 14 December 2023 · filed 15 December 2023
- exercised options over 78,983 shares of Flywire (a derivative holding)SEC Form 415 December 2023Employee Stock Option (right to buy) · traded 14 December 2023 · filed 15 December 2023
- exercised options over 739,821 shares of Flywire (a derivative holding)SEC Form 415 December 2023Employee Stock Option (right to buy) · traded 14 December 2023 · filed 15 December 2023
- exercised options over 93,938 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- exercised options over 40,815 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- had shares withheld for tax on 20,268 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- exercised options over 78,983 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- had shares withheld for tax on 38,808 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- exercised options over 739,821 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- had shares withheld for tax on 411,464 shares of FlywireSEC Form 415 December 2023Voting Common Stock · traded 14 December 2023 · filed 15 December 2023
- ▼ sold on the open market 7,679 shares of FlywireSEC Form 47 December 2023Voting Common Stock · traded 5 December 2023 · filed 7 December 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 419 October 2023Voting Common Stock · traded 17 October 2023 · filed 19 October 2023
- ▼ sold on the open market 10,749 shares of FlywireSEC Form 419 October 2023Voting Common Stock · traded 18 October 2023 · filed 19 October 2023
- ▼ sold on the open market 10,857 shares of FlywireSEC Form 46 October 2023Voting Common Stock · traded 4 October 2023 · filed 6 October 2023
- ▼ sold on the open market 600 shares of FlywireSEC Form 46 October 2023Voting Common Stock · traded 4 October 2023 · filed 6 October 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 46 October 2023Voting Common Stock · traded 5 October 2023 · filed 6 October 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 420 September 2023Voting Common Stock · traded 18 September 2023 · filed 20 September 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 420 September 2023Voting Common Stock · traded 19 September 2023 · filed 20 September 2023
- ▼ sold on the open market 7,742 shares of FlywireSEC Form 47 September 2023Voting Common Stock · traded 5 September 2023 · filed 7 September 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 47 September 2023Voting Common Stock · traded 5 September 2023 · filed 7 September 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 47 September 2023Voting Common Stock · traded 6 September 2023 · filed 7 September 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 431 August 2023Voting Common Stock · traded 29 August 2023 · filed 31 August 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 431 August 2023Voting Common Stock · traded 30 August 2023 · filed 31 August 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 421 August 2023Voting Common Stock · traded 17 August 2023 · filed 21 August 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 421 August 2023Voting Common Stock · traded 18 August 2023 · filed 21 August 2023
- exercised options over 35,750 shares of Flywire (a derivative holding)SEC Form 43 August 2023Stock Option (right to buy) · traded 1 August 2023 · filed 3 August 2023
- exercised options over 35,750 shares of FlywireSEC Form 43 August 2023Voting Common Stock · traded 1 August 2023 · filed 3 August 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 414 July 2023Voting Common Stock · traded 12 July 2023 · filed 14 July 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 414 July 2023Voting Common Stock · traded 13 July 2023 · filed 14 July 2023
- ▼ sold on the open market 7,622 shares of FlywireSEC Form 47 July 2023Voting Common Stock · traded 5 June 2023 · filed 7 July 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 46 July 2023Voting Common Stock · traded 3 July 2023 · filed 6 July 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 46 July 2023Voting Common Stock · traded 5 July 2023 · filed 6 July 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 415 June 2023Voting Common Stock · traded 13 June 2023 · filed 15 June 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 415 June 2023Voting Common Stock · traded 14 June 2023 · filed 15 June 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 47 June 2023Voting Common Stock · traded 5 June 2023 · filed 7 June 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 47 June 2023Voting Common Stock · traded 6 June 2023 · filed 7 June 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 41 June 2023Voting Common Stock · traded 30 May 2023 · filed 1 June 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 41 June 2023Voting Common Stock · traded 31 May 2023 · filed 1 June 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 418 May 2023Voting Common Stock · traded 16 May 2023 · filed 18 May 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 418 May 2023Voting Common Stock · traded 17 May 2023 · filed 18 May 2023
- ▼ sold on the open market 25,740 shares of FlywireSEC Form 413 April 2023Voting Common Stock · traded 11 April 2023 · filed 13 April 2023
- ▼ sold on the open market 50 shares of FlywireSEC Form 413 April 2023Voting Common Stock · traded 11 April 2023 · filed 13 April 2023
- ▼ sold on the open market 11,457 shares of FlywireSEC Form 413 April 2023Voting Common Stock · traded 12 April 2023 · filed 13 April 2023
- ▼ sold on the open market 27,138 shares of FlywireSEC Form 45 April 2023Voting Common Stock · traded 3 April 2023 · filed 5 April 2023
- ▼ sold on the open market 19,033 shares of FlywireSEC Form 45 April 2023Voting Common Stock · traded 4 April 2023 · filed 5 April 2023
- ▼ sold on the open market 24,296 shares of FlywireSEC Form 430 March 2023Voting Common Stock · traded 28 March 2023 · filed 30 March 2023
- ▼ sold on the open market 8,332 shares of FlywireSEC Form 430 March 2023Voting Common Stock · traded 29 March 2023 · filed 30 March 2023
- ▼ sold on the open market 2,000 shares of FlywireSEC Form 430 March 2023Voting Common Stock · traded 29 March 2023 · filed 30 March 2023
- ▼ sold on the open market 4,166 shares of FlywireSEC Form 415 March 2023Voting Common Stock · traded 13 March 2023 · filed 15 March 2023
- was granted 284,436 shares of FlywireSEC Form 415 March 2023Voting Common Stock · traded 14 March 2023 · filed 15 March 2023
- ▼ sold on the open market 4,166 shares of FlywireSEC Form 415 March 2023Voting Common Stock · traded 14 March 2023 · filed 15 March 2023
- ▼ sold on the open market 700 shares of FlywireSEC Form 415 March 2023Voting Common Stock · traded 14 March 2023 · filed 15 March 2023
- ▼ sold on the open market 22,013 shares of FlywireSEC Form 415 March 2023Voting Common Stock · traded 14 March 2023 · filed 15 March 2023
- ▼ sold on the open market 4,666 shares of FlywireSEC Form 414 February 2023Voting Common Stock · traded 10 February 2023 · filed 14 February 2023
- ▼ sold on the open market 4,166 shares of FlywireSEC Form 414 February 2023Voting Common Stock · traded 13 February 2023 · filed 14 February 2023
- ▼ sold on the open market 49,202 shares of FlywireSEC Form 46 February 2023Voting Common Stock · traded 2 February 2023 · filed 6 February 2023
- ▼ sold on the open market 10,732 shares of FlywireSEC Form 46 February 2023Voting Common Stock · traded 3 February 2023 · filed 6 February 2023
- ▼ sold on the open market 4,166 shares of FlywireSEC Form 413 January 2023Voting Common Stock · traded 11 January 2023 · filed 13 January 2023
- ▼ sold on the open market 4,166 shares of FlywireSEC Form 413 January 2023Voting Common Stock · traded 12 January 2023 · filed 13 January 2023
- ▼ sold on the open market 20,862 shares of FlywireSEC Form 45 January 2023Voting Common Stock · traded 3 January 2023 · filed 5 January 2023
- ▼ sold on the open market 4,166 shares of FlywireSEC Form 45 January 2023Voting Common Stock · traded 4 January 2023 · filed 5 January 2023
- exercised options over 12,500 shares of Flywire (a derivative holding)SEC Form 427 December 2022Employee Stock Option (right to buy) · traded 22 December 2022 · filed 27 December 2022
- gave away 25,000 shares of FlywireSEC Form 427 December 2022Voting Common Stock · traded 19 December 2022 · filed 27 December 2022
- exercised options over 12,500 shares of FlywireSEC Form 427 December 2022Voting Common Stock · traded 22 December 2022 · filed 27 December 2022
- ▼ sold on the open market 4,830 shares of FlywireSEC Form 45 October 2022Voting Common Stock · traded 3 October 2022 · filed 5 October 2022
- ▼ sold on the open market 4,830 shares of FlywireSEC Form 45 October 2022Voting Common Stock · traded 4 October 2022 · filed 5 October 2022
- ▼ sold on the open market 4,830 shares of FlywireSEC Form 422 September 2022Voting Common Stock · traded 20 September 2022 · filed 22 September 2022
- ▼ sold on the open market 4,830 shares of FlywireSEC Form 422 September 2022Voting Common Stock · traded 21 September 2022 · filed 22 September 2022
Positions come from the unitedstates/congress-legislators roster, the Office of Government Ethics and the SEC’s Form 4 index. Every disclosed line names its own source and links the document the government published; we print what the filing says and never a price we did not read from it. Headlines and links come from the GDELT Global Knowledge Graph — the story stays with the publisher. The portrait, where we have one, is the public-domain Congressional Bioguide photograph.