Insider Transactions Reported by 26 Insiders of Flywire Corp

Symbol: FLYW on Nasdaq
Location: Boston, MA

Key facts

FLYW - Flywire Corp has 26 insiders with reported activity on this page.
Net insider value flow over the last year: -$2,170,832.
Recent transaction rows are available for direct filing-level review.

Change

Buy value: $3,478,073; sell value: $5,648,904.
Net share flow: -147,517.

Research use

This page gives a plain-language issuer insider context before you inspect transaction-level evidence.
Use the filing links below to verify timestamps, codes, and ownership impacts directly from SEC forms.

Evidence

Filed on Form 4

Issuer insider activity is sourced from SEC Forms 3, 4, and 5.

See Original Filing

Insider trading overview

Last 12 months

Net insider flow leans to selling over the last 12 months. Net value: -$2,170,832.

Buys

$3,478,073

Shares: 251,112

Insiders: 1

Sells

$5,648,904

Shares: 398,629

Insiders: 6

Net

-$2,170,832

Shares: -147,517

Insiders: -5

Window (months)	Buy shares	Sell shares	Buy $	Sell $	Net $
0-3	0	329,511	$0	$4,733,811	-$4,733,811
3-6	251,112	38,426	$3,478,073	$567,295	+$2,910,777
6-9	0	10,663	$0	$142,207	-$142,207
9-12	0	20,029	$0	$205,591	-$205,591

Flywire Corp executives and other stock owners filed with the SEC include:

Name	Relationship	Holdings Value	Past Year Net Change	Change %	Valuation	Report Date
Ossa Investments Pte. Ltd.	10%+ Owner	$216,008,488			Mixed	28 May 2021
Enrique T. Salem	10%+ Owner	$178,634,330			Mixed	11 May 2023
Ajay Agarwal	10%+ Owner	$178,634,330			Mixed	11 May 2023
BAIN CAPITAL VENTURE INVESTORS, LLC	10%+ Owner	$178,634,330			Mixed	11 May 2023
FMR LLC	Other*	$135,059,447			Mixed	28 May 2021
Michael Massaro	Chief Executive Officer, Director	$49,559,381	-$2,665,826	-5.1%	Mixed	06 May 2026
Voss Capital, LP	10%+ Owner	$30,231,140	+$3,478,073	+13%	Mixed	13 Feb 2026
David R. King	Chief Product Officer & Co-President of Global Education	$19,496,676			Mixed	31 Mar 2026
Cosmin Pitigoi	Chief Financial Officer	$15,589,028	-$1,028,174	-6.2%	Filing P/S	06 May 2026
Rob Orgel	President and COO	$12,802,961			Mixed	02 Mar 2026
Peter Butterfield	General Counsel and CCO	$12,097,419	-$694,356	-5.4%	Filing P/S	07 May 2026
Mohit Kansal	Chief Payments Officer	$9,027,924	-$256,006	-2.8%	Filing P/S	06 May 2026
Jo Natauri	Director	$8,147,925			Mixed	12 Dec 2022
GOLDMAN SACHS GROUP INC	Director	$8,147,925			Mixed	12 Dec 2022
Michael G. Ellis	Chief Financial Officer	$7,605,512			Mixed	15 Feb 2024
Alex Finkelstein	Director	$6,984,385			Mixed	03 Jun 2025
Phillip John Riese	Director	$4,103,979	-$897,163	-18%	Filing P/S	06 May 2026
Patrick Blanc	Chief Technology Officer	$3,091,888			Mixed	23 Feb 2026
Diane E. Offereins	Director	$1,036,481			Mixed	03 Jun 2025
Gretchen Howard	Director	$900,997			Mixed	03 Jun 2025
Christine Katziff	Director	$399,666			Mixed	25 Mar 2026
Carleigh Jaques	Director	$361,793			Mixed	03 Jun 2025
Spark Management Partners II, LLC	10%+ Owner	$357,781			Mixed	12 May 2022
Yvonne Hao	Director	$332,333			Mixed	31 May 2022
Matthew C. Harris	Director	$304,761			Mixed	03 Jun 2025
Edwin J. Santos	Director	$178,395	-$107,379	-38%	Filing P/S	05 Jun 2025

Top shareholders of Flywire Corp (13F + 13D/G + 3/4/5)

Grouped by holder across the latest SEC ownership disclosures. Ownership % is shown only when it is directly reported or safely comparable across share classes.

Methodology: rows are grouped by holder and ranked first by SEC-reported ownership % when it is safely comparable, then by disclosed holdings value. — indicates unavailable or non-comparable values; "mixed-class rows" means the latest filing spans non-comparable classes.

Holder	Source	Role / Reporting	Ownership %	Shares	Holdings Value	12M Net Δ	As of	Details
Voss Capital, LP	13D/G 3/4/5 13F	10%+ Owner · Company	12%	14,379,500	$167,375,942	+$23,972,374	31 Mar 2026	13D/G 3/4/5 13F
CADIAN CAPITAL MANAGEMENT, LP	13F 13D/G	Company	5.5% from 13D/G	6,618,119	$77,034,905	—	31 Mar 2026	13F 13D/G
Temasek Holdings (Private) Ltd	13D/G 13F	Temasek Holdings (Private) Limited · Company	5.1%	6,173,385	$87,421,922	$0	31 Dec 2025	13D/G 13F
FMR LLC	3/4/5 13D/G 13F	Other* · Company	1.6% from 13D/G	7,268,490	$135,059,447	—	28 May 2021	3/4/5 13D/G 13F
WILLIAM BLAIR INVESTMENT MANAGEMENT, LLC	13D/G	—	1.2%	1,497,586	$13,208,709	$0	31 Mar 2025	13D/G
Rob Orgel	3/4/5	President and COO	0.95%	1,138,041	$12,802,961	—	02 Mar 2026	3/4/5
Cosmin Pitigoi	3/4/5	Chief Financial Officer	0.75%	897,138	$15,589,028	-$1,028,174	06 May 2026	3/4/5
Peter Butterfield	3/4/5	General Counsel and CCO	0.56%	671,482	$12,097,419	-$694,356	07 May 2026	3/4/5
Mohit Kansal	3/4/5	Chief Payments Officer	0.47%	567,794	$9,027,924	-$256,006	06 May 2026	3/4/5
Patrick Blanc	3/4/5	Chief Technology Officer	0.19%	234,234	$3,091,888	—	23 Feb 2026	3/4/5
Carleigh Jaques	3/4/5	Director	0.03%	32,594	$361,793	—	03 Jun 2025	3/4/5
Christine Katziff	3/4/5	Director	0.02%	28,225	$399,666	—	25 Mar 2026	3/4/5
Matthew C. Harris	3/4/5	Director	0.02%	27,456	$304,761	—	03 Jun 2025	3/4/5
Edwin J. Santos	3/4/5	Director	0.01%	16,990	$178,395	-$107,379	05 Jun 2025	3/4/5
BlackRock, Inc.	13F	Company	7.2%	8,664,019	$100,849,181	—	31 Mar 2026	13F
Divisadero Street Capital Management, LP	13F	Company	5%	6,070,594	$70,661,714	—	31 Mar 2026	13F
JENNISON ASSOCIATES LLC	13F	Company	4.4%	5,298,881	$61,678,976	—	31 Mar 2026	13F
WELLINGTON MANAGEMENT GROUP LLP	13F	Company	4.4%	5,275,581	$61,407,763	—	31 Mar 2026	13F
VANGUARD CAPITAL MANAGEMENT LLC	13F	Company	4.2%	5,044,165	$58,714,081	—	31 Mar 2026	13F
VANGUARD PORTFOLIO MANAGEMENT LLC	13F	Company	4.1%	4,976,560	$57,927,158	—	31 Mar 2026	13F
CITADEL ADVISORS LLC	13F	Company	2.8%	3,386,283	$39,416,334	—	31 Mar 2026	13F
MANGROVE PARTNERS IM, LLC	13F	Company	2.5%	3,014,997	$35,094,565	—	31 Mar 2026	13F
GEODE CAPITAL MANAGEMENT, LLC	13F	Company	2.5%	2,994,302	$34,859,677	—	31 Mar 2026	13F
STATE STREET CORP	13F	Company	2.4%	2,863,556	$33,331,792	—	31 Mar 2026	13F
DIMENSIONAL FUND ADVISORS LP	13F	Company	1.6%	1,886,865	$21,961,619	—	31 Mar 2026	13F
BALYASNY ASSET MANAGEMENT L.P.	13F	Company	1.4%	1,732,342	$20,164,461	—	31 Mar 2026	13F
AMERIPRISE FINANCIAL INC	13F	Company	1.3%	1,578,958	$18,379,072	—	31 Mar 2026	13F
MORGAN STANLEY	13F	Company	1.3%	1,511,092	$17,589,141	—	31 Mar 2026	13F
PRIMECAP MANAGEMENT CO/CA/	13F	Company	1.2%	1,473,500	$17,151,540	—	31 Mar 2026	13F
Ararat Capital Management LP	13F	Company	1.2%	1,444,784	$16,817,286	—	31 Mar 2026	13F
GOLDMAN SACHS GROUP INC	13F 3/4/5	Company · Director	1.2%	1,418,865	$16,515,589	—	31 Mar 2026	13F 3/4/5
FRANKLIN RESOURCES INC	13F	Company	0.99%	1,190,462	$13,856,974	—	31 Mar 2026	13F
COOPER CREEK PARTNERS MANAGEMENT LLC	13F	Company	0.95%	1,139,818	$13,267,000	—	31 Mar 2026	13F
North Reef Capital Management LP	13F	Company	0.91%	1,100,000	$12,804,000	—	31 Mar 2026	13F
NORTHERN TRUST CORP	13F	Company	0.85%	1,027,036	$11,954,700	—	31 Mar 2026	13F
Nuveen, LLC	13F	Company	0.84%	1,014,766	$11,811,876	—	31 Mar 2026	13F
Karl Kapital LLC	13F	Company	0.83%	1,004,580	$11,693,311	—	31 Mar 2026	13F
GDS Wealth Management	13F	Company	0.78%	940,160	$10,943,462	—	31 Mar 2026	13F
D. E. Shaw & Co., Inc.	13F	Company	0.77%	926,956	$10,789,768	—	31 Mar 2026	13F
MARSHALL WACE, LLP	13F	Company	0.77%	925,285	$10,770,318	—	31 Mar 2026	13F
CHARLES SCHWAB INVESTMENT MANAGEMENT INC	13F	Company	0.77%	921,610	$10,727,540	—	31 Mar 2026	13F
Point72 Asset Management, L.P.	13F	Company	0.76%	909,433	$10,585,800	—	31 Mar 2026	13F
PALISADE CAPITAL MANAGEMENT, LP	13F	Company	0.74%	895,862	$10,427,834	—	31 Mar 2026	13F
RENAISSANCE TECHNOLOGIES LLC	13F	Company	0.74%	887,200	$10,327,008	—	31 Mar 2026	13F
BANK OF AMERICA CORP /DE/	13F	Company	0.69%	833,871	$9,706,259	—	31 Mar 2026	13F
First Eagle Investment Management, LLC	13F	Company	0.67%	800,837	$9,321,743	—	31 Mar 2026	13F
Pillsbury Lake Capital LLC	13F	Company	0.64%	771,376	$8,978,817	—	31 Mar 2026	13F
VANGUARD FIDUCIARY TRUST CO	13F	Company	0.64%	769,539	$8,957,434	—	31 Mar 2026	13F
AQR CAPITAL MANAGEMENT LLC	13F	Company	0.61%	739,575	$8,608,652	—	31 Mar 2026	13F
JANE STREET GROUP, LLC	13F	Company	0.53%	631,823	$7,354,420	—	31 Mar 2026	13F

Recent Insider Transactions by Companies or Individuals for Flywire Corp

Showing up to 300 most recent insider transactions from the last 12 months.

Insider	Symbol	Class	Transaction	%	Value $	* Price $	Shares	Shares Owned	Date	Ownership
Peter Butterfield	FLYW	Voting Common Stock	Sale	-0.22%	$26,664	$18.02	-1,480	671,482	07 May 2026	Direct
Michael Massaro	FLYW	Voting Common Stock	Sale	-1.78%	$819,686	$16.39	-50,000	2,766,035	06 May 2026	Direct
Phillip John Riese	FLYW	Voting Common Stock	Sale	-13.9%	$639,598	$16.87	-37,921	234,493	06 May 2026	Direct
Phillip John Riese	FLYW	Voting Common Stock	Options Exercise	16.2%			37,921	272,414	06 May 2026	Direct
Phillip John Riese	FLYW	Stock Option (right to buy)	Options Exercise	-41.7%			-37,921	53,000	06 May 2026	Direct
Cosmin Pitigoi	FLYW	Voting Common Stock	Sale	-3.75%	$608,174	$17.38	-35,000	897,138	06 May 2026	Direct
Mohit Kansal	FLYW	Voting Common Stock	Sale	-2.76%	$256,006	$15.90	-16,101	567,794	06 May 2026	Direct
Cosmin Pitigoi	FLYW	Voting Common Stock	Sale	-3.12%	$420,000	$14.00	-30,000	932,138	21 Apr 2026	Direct
David R. King	FLYW	Voting Common Stock	Options Exercise	0.73%			8,000	1,100,680	31 Mar 2026	Direct
David R. King	FLYW	Employee Stock Option (right to buy)	Options Exercise	-61%			-8,000	5,125	31 Mar 2026	Direct
Peter Butterfield	FLYW	Voting Common Stock	Options Exercise	26.3%			140,000	672,962	30 Mar 2026	Direct
Peter Butterfield	FLYW	Stock Option (right to buy)	Options Exercise	-100%			-140,000	0	30 Mar 2026	Direct
Christine Katziff	FLYW	Voting Common Stock	Award				28,225	28,225	25 Mar 2026	Direct
Michael Massaro	FLYW	Voting Common Stock	Options Exercise	0.5%			14,087	2,816,035	16 Mar 2026	Direct
Michael Massaro	FLYW	Employee Stock Option (right to buy)	Options Exercise	-2.52%			-14,087	544,326	16 Mar 2026	Direct
Peter Butterfield	FLYW	Voting Common Stock	Sale	-1.66%	$117,543	$13.05	-9,009	532,962	05 Mar 2026	Direct
Mohit Kansal	FLYW	Voting Common Stock	Tax liability	-3.34%			-20,181	583,895	02 Mar 2026	Direct
Michael Massaro	FLYW	Voting Common Stock	Tax liability	-3.61%			-105,021	2,801,948	02 Mar 2026	Direct
Michael Massaro	FLYW	Voting Common Stock	Sale	-4.91%	$1,846,140	$12.31	-150,000	2,906,969	02 Mar 2026	Direct
Cosmin Pitigoi	FLYW	Voting Common Stock	Tax liability	-3.96%			-39,722	962,138	02 Mar 2026	Direct
David R. King	FLYW	Voting Common Stock	Tax liability	-3.09%			-34,811	1,092,680	02 Mar 2026	Direct
Peter Butterfield	FLYW	Voting Common Stock	Tax liability	-2.54%			-14,121	541,971	02 Mar 2026	Direct
Rob Orgel	FLYW	Voting Common Stock	Tax liability	-5.36%			-64,512	1,138,041	02 Mar 2026	Direct
Michael Massaro	FLYW	Voting Common Stock	Award	32.6%			751,811	3,056,969	24 Feb 2026	Direct
Rob Orgel	FLYW	Voting Common Stock	Award	43.1%			362,318	1,202,553	24 Feb 2026	Direct
Peter Butterfield	FLYW	Voting Common Stock	Award	48.3%			181,159	556,092	24 Feb 2026	Direct
Cosmin Pitigoi	FLYW	Voting Common Stock	Award	56.6%			362,318	1,001,860	24 Feb 2026	Direct
David R. King	FLYW	Voting Common Stock	Award	27.7%			244,565	1,127,491	24 Feb 2026	Direct
Patrick Blanc	FLYW	Voting Common Stock	Award				234,234	234,234	23 Feb 2026	Direct
Voss Capital, LP	FLYW	Voting common stock, $0.0001 par value per share	Purchase	1.1%	$274,795	$10.99	25,000	2,300,000	13 Feb 2026	By: By: Voss Value Master Fund, L.P.
Peter Butterfield	FLYW	Voting Common Stock	Sale	-3.43%	$200,073	$15.01	-13,327	374,933	07 Jan 2026	Direct
Phillip John Riese	FLYW	Voting Common Stock	Sale	-6.62%	$250,559	$15.08	-16,612	234,493	07 Jan 2026	Direct
Phillip John Riese	FLYW	Voting Common Stock	Options Exercise	7.08%			16,612	251,105	07 Jan 2026	Direct
Phillip John Riese	FLYW	Stock Option (right to buy)	Options Exercise	-15.4%			-16,612	90,921	07 Jan 2026	Direct
Voss Capital, LP	FLYW	Voting common stock, $0.0001 par value per share	Purchase	0.47%	$640,415	$14.23	44,991	9,670,000	31 Dec 2025	By: Managed Accounts of Voss Capital, LP
Voss Capital, LP	FLYW	Voting common stock, $0.0001 par value per share	Purchase	1.92%	$2,562,862	$14.15	181,121	9,625,009	30 Dec 2025	By: Managed Accounts of Voss Capital, LP
Peter Butterfield	FLYW	Voting Common Stock	Options Exercise	1.56%			5,950	388,260	30 Dec 2025	Direct
Peter Butterfield	FLYW	Stock Option (right to buy)	Options Exercise	-4.08%			-5,950	140,000	30 Dec 2025	Direct
Michael Massaro	FLYW	Voting Common Stock	Gift	25.3%			465,043	2,305,158	24 Dec 2025	Direct
Michael Massaro	FLYW	Voting Common Stock	Gift	-70.8%			-465,043	192,193	24 Dec 2025	See footnote
Phillip John Riese	FLYW	Voting Common Stock	Sale	-0.16%	$5,505	$15.00	-367	234,493	23 Dec 2025	Direct
Phillip John Riese	FLYW	Voting Common Stock	Options Exercise	0.16%			367	234,860	23 Dec 2025	Direct
Phillip John Riese	FLYW	Stock Option (right to buy)	Options Exercise	-0.34%			-367	107,533	23 Dec 2025	Direct
Peter Butterfield	FLYW	Voting Common Stock	Sale	-2.08%	$111,159	$13.69	-8,120	382,310	09 Dec 2025	Direct
Peter Butterfield	FLYW	Voting Common Stock	Tax liability	-1.15%			-4,524	388,998	01 Dec 2025	Direct
Cosmin Pitigoi	FLYW	Voting Common Stock	Tax liability	-2.04%			-13,340	639,542	01 Dec 2025	Direct
David R. King	FLYW	Voting Common Stock	Tax liability	-1.2%			-10,725	881,683	01 Dec 2025	Direct
Rob Orgel	FLYW	Voting Common Stock	Tax liability	-1.68%			-14,332	838,992	01 Dec 2025	Direct
Michael Massaro	FLYW	Voting Common Stock	Tax liability	-1.42%			-26,514	1,838,872	01 Dec 2025	Direct
Phillip John Riese	FLYW	Voting Common Stock	Sale	-0.04%	$1,502	$15.02	-100	234,493	05 Nov 2025	Direct

* An asterisk sign (*) next to the price indicates that the price is likely invalid.