FLYWFlywire Corp · Insider ownership research

Flywire Corp insiders sold $17.9M in the past 12 months. How much of their stake is that?

95% was sold under disclosed trading plans, 5% with no plan disclosed. The largest seller, Michael Massaro (Chief Executive Officer, Director), sold $7.8M.Share-of-stake figures for this company are being verified and will be added when that check is finished. Why

Updated Oct 16, 2026 from SEC filings · covers Oct 17, 2025 to Oct 16, 2026

$902K

sold with no plan disclosed, past 12 months

95%

of sales were under disclosed trading plans, past 12 months

8 of 16

officers and directors sold shares, past 12 months

Is this normal? In line with the past 4 years. 8 insiders sold; the average is 6 a year. Year by year

Latest filing: Filed Oct 15 for a sale on Oct 13. David King sold 37K shares ($676K) under a disclosed plan. Filing

SEC ownership filings: 81 filed in the 12 months to Oct 16, 2026; 479 on record since May 25, 2021 · See the evidence

Price note. One filing reports a price of $409,131.00, about 9705 times the same filer's other prices that week; it appears to be an error in the filing, so we've excluded it from totals. Filing

What stands out

Routine activity: 95% of sales were under disclosed plans, and no insider sold more than 1% of vested holdings.

A share of stake is shown for 0 of the 8 officers and directors who sold. 16 are left out

i

Left out: Michael Massaro, David King, Rob Orgel, Cosmin Pitigoi, Peter Butterfield, Alex Finkelstein, Phillip Riese, Mohit Kansal, Gretchen Howard, Diane Offereins, Carleigh Jaques, Matthew Harris, Edwin Santos, Patrick Blanc, Christine Katziff and Sabrina Farmer (share of stake is being verified).

Disclosed company stock is not an insider's whole wealth.

Who sold, and how much of their stake

Officers and directors, past 12 months. Their share of stake is being verified and is not shown yet; amounts and trading plans are below.

Michael Massaro

Chief Executive Officer, Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$7.8MDisclosed plan

Rob Orgel

President and COO

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$3.0MDisclosed plan

Phillip Riese

Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$1.6M60% planned 40% no plan disclosed

Peter Butterfield

General Counsel and CCO

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$1.4MDisclosed plan

Mohit Kansal

Chief Payments Officer

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$1.4MDisclosed plan

Selling by month

Officers and directors, Oct 2025 to Oct 2026. Each sale is counted once: under a disclosed plan, else to cover taxes, else no plan disclosed.

Disclosed planNo plan disclosedOne dollar scale for every month; the tallest bar is labeled

Recent activity

Past 30 days, Sep 17, 2026 to Oct 16, 2026

Oct 13, 2026David King sold 37K shares ($676K) under a disclosed trading plan.

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
David King Chief Product Officer & Co-President of Global Education	36,900	$18.32	n/a	n/a	Oct 13, 2026	Oct 15, 2026

"% of total stake" is the shares in an event against all the vested shares the person held that day, across every share class and holding entity, after that day's vesting. "n/a" means the person's holdings are not confirmed, or the row is a purchase. "Holdings record incomplete" means more shares were sold than the filings show the person held that day, so a percentage would be wrong.

Outside holders, reported separately

Voss Capital, LP sold $10.3M in the past 12 months. Large shareholders and the funds or companies that board members represent are not part of management, so they are left out of the figures above.

Common questions

Is the Flywire Corp CEO selling stock?

Yes. Michael Massaro sold 488K shares ($7.8M) in the past 12 months, all of it under a trading plan disclosed in the filings.

Why are Flywire Corp insiders selling?

Filings rarely give a reason, and we don't guess at one. What they show is how the sales were made: 95% of sales by value ran under 10b5-1 trading plans disclosed in the filings and 5% had no disclosed plan. A trading plan schedules sales in advance.

Are any Flywire Corp insiders buying?

No. Officers and directors reported no purchases in the past 12 months.

The evidence

Who sold8 officers and directors: amount, % of holdings, trading plan

Who sold	Amount	% of holdings	Trading plan
Michael Massaro Chief Executive Officer, Director	$7.8M 488K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Rob Orgel President and COO	$3.0M 179K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Phillip Riese Director	$1.6M 96K shares	Not confirmed share of stake is being verified. Why	60% under a disclosed plan 40% no plan disclosed
Peter Butterfield General Counsel and CCO	$1.4M 89K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Mohit Kansal Chief Payments Officer	$1.4M 87K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
David King Chief Product Officer & Co-President of Global Education	$1.3M 74K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Cosmin Pitigoi Chief Financial Officer	$1.0M 65K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Edwin Santos Director	$246K 17K shares	Not confirmed share of stake is being verified. Why	No plan disclosed

Board members representing outside shareholders, reported separately: Alex Finkelstein, Matthew Harris. Details

Outside holder, reported separately: Voss Capital, LP (a 10% owner, not part of management). Sold $10.3M (544K shares) from Aug 18, 2026 to Aug 28, 2026. Latest filing

The full ownership picture0 of 16 officers and directors confirmed

Vested shares across all share classes, held directly and through trusts, LLCs and family members, as reported on SEC Forms 3, 4 and 5. Unvested awards and options are never counted as owned shares.

Insider

Held Oct 16, 2025

Sold

Held Oct 16, 2026

Still held

Michael Massaro

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Michael Massaro are complete.

Chief Executive Officer, Director

n/a

−488K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Michael Massaro

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Michael Massaro are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−211Kwithheld by the company for taxes

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
544,326	$3.95	Apr 29, 2025	$7.8M

Estimate: options held × ($18.32 − strike price), using the most recent insider trade price on Form 4 (Oct 13, 2026), not a market close.

David King

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for David King are complete.

Chief Product Officer & Co-President of Global Education

n/a

−74K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for David King

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for David King are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−77Kwithheld by the company for taxes

Rob Orgel

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Rob Orgel are complete.

President and COO

n/a

−179K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Rob Orgel

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Rob Orgel are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−123Kwithheld by the company for taxes

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
234,663	$3.95	Jan 20, 2031	$3.4M
384,452	$3.30	Nov 1, 2029	$5.8M

Estimate: options held × ($18.32 − strike price), using the most recent insider trade price on Form 4 (Oct 13, 2026), not a market close.

Cosmin Pitigoi

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Cosmin Pitigoi are complete.

Chief Financial Officer

n/a

−65K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Cosmin Pitigoi

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Cosmin Pitigoi are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−94Kwithheld by the company for taxes

Peter Butterfield

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Peter Butterfield are complete.

General Counsel and CCO

n/a

−89K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Peter Butterfield

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Peter Butterfield are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−34Kwithheld by the company for taxes

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
90	$0.35	Mar 10, 2025	$2K
73,794	$3.95	Jan 20, 2031	$1.1M
69,607	$3.95	Jan 20, 2031	$1.0M

Estimate: options held × ($18.32 − strike price), using the most recent insider trade price on Form 4 (Oct 13, 2026), not a market close.

Alex Finkelstein

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Alex Finkelstein are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Alex Finkelstein

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Alex Finkelstein are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Phillip Riese

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Phillip Riese are complete.

Director

n/a

−96K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Phillip Riese

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Phillip Riese are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Mohit Kansal

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Mohit Kansal are complete.

Chief Payments Officer

n/a

−87K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Mohit Kansal

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Mohit Kansal are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−40Kwithheld by the company for taxes

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
11,989	$3.95	Jan 20, 2031	$172K

Estimate: options held × ($18.32 − strike price), using the most recent insider trade price on Form 4 (Oct 13, 2026), not a market close.

Gretchen Howard

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Gretchen Howard are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Gretchen Howard

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Gretchen Howard are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Diane Offereins

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Diane Offereins are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Diane Offereins

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Diane Offereins are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Carleigh Jaques

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Carleigh Jaques are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Carleigh Jaques

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Carleigh Jaques are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Matthew Harris

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Matthew Harris are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Matthew Harris

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Matthew Harris are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Edwin Santos

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Edwin Santos are complete.

Director

n/a

−17K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Edwin Santos

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Edwin Santos are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Patrick Blanc

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Patrick Blanc are complete.

Chief Technology Officer

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Patrick Blanc

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Patrick Blanc are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Christine Katziff

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Christine Katziff are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Christine Katziff

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Christine Katziff are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Sabrina Farmer

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Sabrina Farmer are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Sabrina Farmer

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Sabrina Farmer are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Holdings and share of stake for Flywire Corp are being verified, so no balances, unit counts or percentages are shown. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings.

What explains the selling$17.9M of sales by plan status, purpose, seller and month

Officer and director open-market sales: $17.9M across 1,093,891 shares. Plan status and stated purpose are separate questions, and a sale can have both.

By plan status

Disclosed plan · $17.0M · 95%

5%

The lighter segment is sales with no plan disclosed in the filing ($902K), including tax-related sales outside a plan.

No plan disclosed · $902K

Sales with no 10b5-1 plan and no tax reference in the filing. $656K of it is Phillip Riese. No plan disclosed is a statement about the filing, not about why the sale happened. Largest such sale: Phillip Riese, Aug 7, 2026

Taxes

579,097 shares ($8.2M) were withheld by the company for taxes, which isn't a market sale.

Seller	Shares sold	Proceeds	Under a disclosed plan	Share of total	Sales dates
Michael Massaro Chief Executive Officer, Director	488K	$7.8M	100%	44%	Mar 2, 2026 to Sep 1, 2026
Rob Orgel President and COO	179K	$3.0M	100%	17%	Jun 1, 2026 to Jun 1, 2026
Phillip Riese Director	96K	$1.6M	60%	9%	Nov 5, 2025 to Aug 7, 2026
Peter Butterfield General Counsel and CCO	89K	$1.4M	100%	8%	Nov 5, 2025 to Sep 8, 2026
Mohit Kansal Chief Payments Officer	87K	$1.4M	100%	8%	May 6, 2026 to Sep 2, 2026
David King Chief Product Officer & Co-President of Global Education	74K	$1.3M	100%	7%	Sep 11, 2026 to Oct 13, 2026
Cosmin Pitigoi Chief Financial Officer	65K	$1.0M	100%	6%	Apr 21, 2026 to May 6, 2026
Edwin Santos Director	17K	$246K	0%	1%	Jun 4, 2026 to Jun 8, 2026

Sales by month

Month	Sale proceeds	Disclosed plan	To cover taxes	No plan disclosed
Oct 2025	$0	$0	$0	$0
Nov 2025	$17K	$17K	$0	$0
Dec 2025	$117K	$117K	$0	$0
Jan 2026	$451K	$451K	$0	$0
Feb 2026	$0	$0	$0	$0
Mar 2026	$2.0M	$2.0M	$0	$0
Apr 2026	$420K	$420K	$0	$0
May 2026	$2.4M	$2.4M	$0	$0
Jun 2026	$5.2M	$5.0M	$0	$246K
Jul 2026	$2.9M	$2.9M	$0	$0
Aug 2026	$656K	$0	$0	$656K
Sep 2026	$3.2M	$3.2M	$0	$0
Oct 2026	$676K	$676K	$0	$0

Board members representing outside shareholders (2)Listed and sourced; not part of the management totals or the answer line

Directors whose reported holdings sit mostly in an investment fund or a corporate shareholder they represent, not in their own name, with beneficial ownership disclaimed except for their own financial interest. Listed and sourced here; not part of the management totals or the answer line. Shares a fund hands to its own investors are distributions, not sales.

Board member	Held Oct 16, 2025	Sold	Held Oct 16, 2026	Still held
Alex Finkelstein ! Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Alex Finkelstein are complete. Director	n/a	0	n/a	n/a
Vesting, gifts, unvested awards and holding lines for Alex Finkelstein Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Alex Finkelstein are complete; balances and unit counts will be added when the check is finished. 0gifted (net of own trusts)
Matthew Harris ! Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Matthew Harris are complete. Director	n/a	0	n/a	n/a
Vesting, gifts, unvested awards and holding lines for Matthew Harris Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Matthew Harris are complete; balances and unit counts will be added when the check is finished. 0gifted (net of own trusts)

Is this normal? Selling year by year4 earlier years to compare with

In line with the past 4 years. 8 insiders sold; the average is 6 a year.

12 months ending	Shares sold	Insiders who sold	Proceeds
Oct 16, 2026 Latest 12 months	1.09M	8	$17.9M
Oct 16, 2025 1 year earlier	40K	2	$485K
Oct 16, 2024 2 years earlier	483K	7	$11.8M
Oct 17, 2023 3 years earlier	1.62M	8	$47.0M
Oct 17, 2022 4 years earlier	940K	8	$28.2M
Oct 17, 2021 5 years earlier · filings don't cover the whole year	n/a	n/a	n/a

Open-market sales (Form 4 code S) by people who were officers or directors, in split-adjusted shares. Earlier years include people who have since left. A sale that an outside holder also reports (a family trust, a fund) is counted with outside holders in every year. Shares, not dollars, are compared, so a change in the stock price doesn't look like a change in selling. Years the filings don't fully cover are shown but left out of the average.

Known gaps and uncertainty16 officers and directors not confirmed

Holdings and share of stake are being verified. Balances, unit counts and every share-of-stake figure for Flywire Corp are held back until that check is finished. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings and are complete.

External context: we only cite outside events when a documented connection exists. None is shown for this period.

Sources and methodology479 filings on record, 81 filed in the 12-month period, and how we read them

All 479 Forms 3, 4 and 5 on record for Flywire Corp (SEC CIK 1580560), filed from May 25, 2021 to Oct 15, 2026; 81 of them were filed in the 12 months this page covers, retrieved from SEC EDGAR on Oct 16, 2026. Prices are the ones reported in each filing, often weighted averages.

Holdings. Each holding line (a share class plus an owner, such as a trust or LLC) carries its last reported balance forward. Entities first reported during the period start at zero, so transfers between an insider's own trusts don't count as selling. Lines not reported for three years or more are listed separately and left out of totals.

Sales. A sale counts as under a 10b5-1 plan if its footnote cites one or the filing's Rule 10b5-1 box is checked, and as tax-related if its footnote cites tax obligations or sell-to-cover. Shares withheld by the company for taxes are listed separately. Sales with neither attribute are labeled "no plan disclosed".

Full methodology

Former or inactive filers (9)No filing in 18 months; last reported balances, not in any total

Name	Last filed	Last reported balance
Michael Ellis	Feb 16, 2024	383,248 shares, last reported balance as of Feb 15, 2024
BAIN CAPITAL VENTURE INVESTORS, LLC	May 15, 2023	32,890,150 shares, last reported balance as of May 11, 2023
Ajay Agarwal	May 15, 2023	8,795,388 shares, last reported balance as of May 11, 2023
Jo Natauri	Dec 14, 2022	5,821,505 shares, last reported balance as of Dec 13, 2022
GOLDMAN SACHS GROUP INC	Dec 14, 2022	5,729,855 shares, last reported balance as of Dec 13, 2022
Yvonne Hao	Jun 2, 2022	16,363 shares, last reported balance as of May 31, 2022
Spark Management Partners II, LLC	May 16, 2022	7,067,601 shares, last reported balance as of May 12, 2022
FMR LLC	Jun 2, 2021	7,460,328 shares, last reported balance as of May 28, 2021
Ossa Investments Pte. Ltd.	Jun 1, 2021	12,508,893 shares, last reported balance as of May 28, 2021

Spotted something wrong on this page? Report an error. We check every report against the SEC filing and list what we fix in the corrections log.