Flywire Corporation (FLYW) Insider Trading

Last 12 months

Insiders sold $17.9M and bought nothing on the open market.

95% of the selling was scheduled in advance under 10b5-1 plans. Director Phillip John Riese sold $656k on Aug 7, 12% of their stake, outside a plan. The last open-market buy by an executive or director was in Feb 2025.

Net open-market

−$17.9M

0 buys · 30 sales

Under a 10b5-1 plan

95%

of the value sold

Insiders who bought / sold

0 / 8

executives and directors

Last open-market buy

Feb 2025

Feb 27, 2025

Get an email when FLYW's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Oct 13	David R. King See Remarks	Sold10b5-1 plan	36,900	$18.32	$676k	2.8%	Form 4
Sep 11	David R. King See Remarks	Sold10b5-1 plan	36,900	$17.88	$660k	2.7%	Form 4
Sep 8	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	12,156	$17.99	$219k	2.0%	Form 4
Sep 2	Mohit Kansal Chief Payments Officer	Sold10b5-1 plan	12,423	$18.69	$232k	2.5%	Form 4
Sep 1	Michael Massaro Chief Executive Officer	Sold10b5-1 plan	112,500	$18.39	$2.07M	4.0%	Form 4
Aug 28	Voss Value-Oriented Special Situations Fund, LP Large holder	SoldNo plan 2 parts	44,768	$18.78 average	$841k	0.3%	Form 4
Aug 26 – 27	Voss Capital, LP Large holder	SoldNo plan 4 parts	120,021	$18.94 average	$2.27M	0.9%	Form 4
Aug 24 – 25	Voss Value Master Fund, LP Large holder	SoldNo plan 4 parts	274,273	$19.30 average	$5.29M	1.9%	Form 4
Aug 18 – 19	Voss Value Master Fund, LP Large holder	SoldNo plan 7 parts	104,500	$18.46 average	$1.93M	0.7%	Form 4
Aug 7	Phillip John Riese Director	SoldNo plan	36,000	$18.22	$656k	12%	Form 4
Jul 16 – 17	Michael Massaro Chief Executive Officer	Sold10b5-1 plan 2 parts	125,000	$18.51 average	$2.31M	4.2%	Form 4
Jul 1	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	31,096	$18.06	$562k	4.8%	Form 4
Jun 25	Mohit Kansal Chief Payments Officer	Sold10b5-1 plan	3,650	$16.96	$62k	0.7%	Form 4
Jun 15	Mohit Kansal Chief Payments Officer	Sold10b5-1 plan	54,543	$15.15	$826k	9.8%	Form 4
Jun 15	Michael Massaro Chief Executive Officer	Sold10b5-1 plan	50,000	$15.26	$763k	1.7%	Form 4
Jun 15	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	6,528	$15.08	$98k	1.0%	Form 4
Jun 8	Edwin J Santos Director	SoldNo plan	6,524	$14.12	$92k	36%	Form 4
Jun 5	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	6,188	$14.40	$89k	0.9%	Form 4
Jun 4	Edwin J Santos Director	SoldNo plan	10,466	$14.69	$154k	37%	Form 4
Jun 2	Phillip John Riese Director	Sold10b5-1 plan 2 parts	5,000	$15.42 average	$77k	2.0%	Form 4
Jun 1	Rob Orgel President and COO	Sold10b5-1 plan	178,980	$17.00	$3.04M	16%	Form 4
May 7	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	1,480	$18.02	$27k	0.2%	Form 4
May 6	Michael Massaro Chief Executive Officer	Sold10b5-1 plan 2 parts	50,000	$16.39 average	$820k	1.6%	Form 4
May 6	Phillip John Riese Director	Sold10b5-1 plan 3 parts	37,921	$16.86 average	$640k	14%	Form 4
May 6	Cosmin Pitigoi Chief Financial Officer	Sold10b5-1 plan	35,000	$17.38	$608k	3.8%	Form 4
May 6	Mohit Kansal Chief Payments Officer	Sold10b5-1 plan	16,101	$15.90	$256k	2.8%	Form 4
Apr 21	Cosmin Pitigoi Chief Financial Officer	Sold10b5-1 plan	30,000	$14.00	$420k	3.1%	Form 4
Mar 5	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	9,009	$13.05	$118k	1.7%	Form 4
Mar 2	Michael Massaro Chief Executive Officer	Sold10b5-1 plan	150,000	$12.31	$1.85M	4.8%	Form 4
Feb 13	Voss Value Master Fund, LP Large holder	Bought	25,000	$10.99	$275k	0.9%	Form 4
Jan 7	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	13,327	$15.01	$200k	3.4%	Form 4
Jan 7	Phillip John Riese Director	Sold10b5-1 plan	16,612	$15.08	$251k	6.6%	Form 4
Dec 30, 2025 – Dec 31, 2025	Voss Value Master Fund, LP Large holder	Bought 2 parts	226,112	$14.17 average	$3.2M	1.9%	Form 4
Nov 5, 2025 – Dec 23, 2025	Phillip John Riese Director	Sold10b5-1 plan 2 parts	467	$15.00 average	$7k	0.2%	Form 4
Dec 9, 2025	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	8,120	$13.69	$111k	2.1%	Form 4
Nov 5, 2025	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	1,000	$15.00	$15k	0.3%	Form 4
Sep 8, 2025	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	9,563	$13.15	$126k	2.4%	Form 4
Jun 9, 2025	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	9,563	$10.27	$98k	2.3%	Form 4
Jun 5, 2025 – Jun 6, 2025	Edwin J Santos Director	SoldNo plan 2 parts	10,466	$10.26 average	$107k	38%	Form 4
Mar 10, 2025	Peter Butterfield General Counsel and CCO	Sold10b5-1 plan	5,523	$10.08	$56k	2.2%	Form 4

Oct 1310b5-1 plan
David R. King
See Remarks · sold 36,900 at $18.32
$676k
2.8% of stake
Sep 1110b5-1 plan
David R. King
See Remarks · sold 36,900 at $17.88
$660k
2.7% of stake
Sep 810b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 12,156 at $17.99
$219k
2.0% of stake
Sep 210b5-1 plan
Mohit Kansal
Chief Payments Officer · sold 12,423 at $18.69
$232k
2.5% of stake
Sep 110b5-1 plan
Michael Massaro
Chief Executive Officer · sold 112,500 at $18.39
$2.07M
4.0% of stake
Aug 28No plan
Voss Value-Oriented Special Situations Fund, LP
Large holder · sold 44,768 at avg $18.78
$841k
0.3% of stake
Aug 26 – 27No plan
Voss Capital, LP
Large holder · sold 120,021 at avg $18.94
$2.27M
0.9% of stake
Aug 24 – 25No plan
Voss Value Master Fund, LP
Large holder · sold 274,273 at avg $19.30
$5.29M
1.9% of stake
Aug 18 – 19No plan
Voss Value Master Fund, LP
Large holder · sold 104,500 at avg $18.46
$1.93M
0.7% of stake
Aug 7No plan
Phillip John Riese
Director · sold 36,000 at $18.22
$656k
12% of stake
Jul 16 – 1710b5-1 plan
Michael Massaro
Chief Executive Officer · sold 125,000 at avg $18.51
$2.31M
4.2% of stake
Jul 110b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 31,096 at $18.06
$562k
4.8% of stake
Jun 2510b5-1 plan
Mohit Kansal
Chief Payments Officer · sold 3,650 at $16.96
$62k
0.7% of stake
Jun 1510b5-1 plan
Mohit Kansal
Chief Payments Officer · sold 54,543 at $15.15
$826k
9.8% of stake
Jun 1510b5-1 plan
Michael Massaro
Chief Executive Officer · sold 50,000 at $15.26
$763k
1.7% of stake
Jun 1510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 6,528 at $15.08
$98k
1.0% of stake
Jun 8No plan
Edwin J Santos
Director · sold 6,524 at $14.12
$92k
36% of stake
Jun 510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 6,188 at $14.40
$89k
0.9% of stake
Jun 4No plan
Edwin J Santos
Director · sold 10,466 at $14.69
$154k
37% of stake
Jun 210b5-1 plan
Phillip John Riese
Director · sold 5,000 at avg $15.42
$77k
2.0% of stake
Jun 110b5-1 plan
Rob Orgel
President and COO · sold 178,980 at $17.00
$3.04M
16% of stake
May 710b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 1,480 at $18.02
$27k
0.2% of stake
May 610b5-1 plan
Michael Massaro
Chief Executive Officer · sold 50,000 at avg $16.39
$820k
1.6% of stake
May 610b5-1 plan
Phillip John Riese
Director · sold 37,921 at avg $16.86
$640k
14% of stake
May 610b5-1 plan
Cosmin Pitigoi
Chief Financial Officer · sold 35,000 at $17.38
$608k
3.8% of stake
May 610b5-1 plan
Mohit Kansal
Chief Payments Officer · sold 16,101 at $15.90
$256k
2.8% of stake
Apr 2110b5-1 plan
Cosmin Pitigoi
Chief Financial Officer · sold 30,000 at $14.00
$420k
3.1% of stake
Mar 510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 9,009 at $13.05
$118k
1.7% of stake
Mar 210b5-1 plan
Michael Massaro
Chief Executive Officer · sold 150,000 at $12.31
$1.85M
4.8% of stake
Feb 13
Voss Value Master Fund, LP
Large holder · bought 25,000 at $10.99
$275k
0.9% of stake
Jan 710b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 13,327 at $15.01
$200k
3.4% of stake
Jan 710b5-1 plan
Phillip John Riese
Director · sold 16,612 at $15.08
$251k
6.6% of stake
Dec 30, 2025 – Dec 31, 2025
Voss Value Master Fund, LP
Large holder · bought 226,112 at avg $14.17
$3.2M
1.9% of stake
Nov 5, 2025 – Dec 23, 202510b5-1 plan
Phillip John Riese
Director · sold 467 at avg $15.00
$7k
0.2% of stake
Dec 9, 202510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 8,120 at $13.69
$111k
2.1% of stake
Nov 5, 202510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 1,000 at $15.00
$15k
0.3% of stake
Sep 8, 202510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 9,563 at $13.15
$126k
2.4% of stake
Jun 9, 202510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 9,563 at $10.27
$98k
2.3% of stake
Jun 5, 2025 – Jun 6, 2025No plan
Edwin J Santos
Director · sold 10,466 at avg $10.26
$107k
38% of stake
Mar 10, 202510b5-1 plan
Peter Butterfield
General Counsel and CCO · sold 5,523 at $10.08
$56k
2.2% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch FLYW, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

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Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

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