What indirect Flywire (FLYW) share holdings are associated with CEO Michael Massaro?

Indirect holdings include 307,548 shares held by the M Massaro Trust and 192,193 shares held by the Michael P. Massaro 2021 Irrevocable Trust. His spouse is trustee of both, and he disclaims beneficial ownership except for any pecuniary interests he may have.

Flywire CEO shares withheld for tax obligations

Flywire Corp Chief Executive Officer Michael Massaro reported a routine tax-related share disposition.

Filing Impact

(Very High)

Filing Sentiment

(Neutral)How Sentiment works

Sentiment and the balance of points

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Form Type

Rhea-AI Filing Summary

Flywire Corp Chief Executive Officer Michael Massaro reported a routine tax-related share disposition. The company withheld 39,799 shares of voting common stock at $16.61 per share to satisfy income tax withholding from the net settlement of time-based restricted stock units, and this was not an open market sale. After this event, he directly holds 2,726,236 shares of voting common stock. Additional shares, including 307,548 held by the M Massaro Trust and 192,193 held by the Michael P. Massaro 2021 Irrevocable Trust, are reported as indirect holdings, with Massaro disclaiming beneficial ownership except for any pecuniary interest.

Insider Trade Summary

Exercise Price or Tax Liability: 39,799 shares

Exercise Price or Tax Liability 3 txns

Insider Massaro Michael

Role Chief Executive Officer

Type	Security	Shares	Price	Value
Exercise Price or Tax Liability	Voting Common Stock	39,799	$16.61	$661K
holding	Voting Common Stock	--	--	--
holding	Voting Common Stock	--	--	--

Holdings After Transaction: Voting Common Stock — 2,726,236 shares (Direct); Voting Common Stock — 499,741 shares (Indirect, See footnote)

Footnotes (3)

F1. Represents the number of shares of common stock that have been withheld by the Issuer to satisfy its income tax withholding and remittance obligations in connection with the net settlement of certain time-based restricted stock unit awards and does not represent an open market sale.
F2. The shares are held by the M Massaro Trust, of which the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16 or for any other purpose, except to the extent of the Reporting Person's pecuniary interests therein, if any.
F3. The shares are held by the Michael P. Massaro 2021 Irrevocable Trust, of which the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16 or for any other purpose, except to the extent of the Reporting Person's pecuniary interests therein, if any.

Key Figures

Tax-withheld shares: 39,799 shares Withholding price: $16.61 per share Direct holdings after transaction: 2,726,236 shares +2 more

5 metrics

Tax-withheld shares 39,799 shares Withheld to satisfy income tax from RSU net settlement

Withholding price $16.61 per share Price for 39,799 tax-withheld voting common shares

Direct holdings after transaction 2,726,236 shares Voting common stock directly held by CEO after withholding

M Massaro Trust holdings 307,548 shares Indirect holdings in trust where spouse is trustee; beneficial ownership disclaimed

2021 Irrevocable Trust holdings 192,193 shares Indirect holdings in Michael P. Massaro 2021 Irrevocable Trust; beneficial ownership disclaimed

Key Terms

restricted stock unit, net settlement, income tax withholding, pecuniary interests, +1 more

5 terms

restricted stock unit financial

"in connection with the net settlement of certain time-based restricted stock unit awards"

A restricted stock unit is a promise from a company to give an employee shares of stock after certain conditions are met, like staying with the company for a set amount of time. It’s like earning a bonus that turns into company stock once you’ve proven your commitment, making it a way to motivate and reward employees.

net settlement financial

"in connection with the net settlement of certain time-based restricted stock unit awards"

income tax withholding financial

"withheld by the Issuer to satisfy its income tax withholding and remittance obligations"

pecuniary interests financial

"except to the extent of the Reporting Person's pecuniary interests therein, if any"

Section 16 regulatory

"shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16"

Section 16 is a U.S. securities law rule that governs the trading and disclosure obligations of company insiders — typically officers, directors and large shareholders — to promote transparency and deter unfair profit-taking. It requires insiders to publicly report their stock trades and allows companies or the issuer to reclaim quick, short-term profits from certain insider trades, like a scoreboard and a refund policy that help investors see and limit possible insider advantage.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Flywire (FLYW) report for CEO Michael Massaro?

Flywire reported that CEO Michael Massaro had 39,799 shares of voting common stock withheld to cover income tax obligations from restricted stock unit settlement. This F‑code transaction is a tax-withholding disposition, not an open market buy or sell of shares.

Was the Flywire (FLYW) CEO’s Form 4 transaction an open market sale?

No, the 39,799 Flywire shares were withheld by the company to satisfy income tax obligations from RSU net settlement. The footnote explicitly states this withholding does not represent an open market sale of voting common stock by the CEO.

How many Flywire (FLYW) shares does CEO Michael Massaro hold directly after this filing?

After the tax-withholding disposition, Michael Massaro directly holds 2,726,236 shares of Flywire voting common stock. This figure reflects his direct ownership position following the withholding of 39,799 shares to cover income tax obligations related to restricted stock units.

What does the F transaction code mean in Flywire (FLYW) CEO’s Form 4?

The F code indicates shares were disposed to pay exercise price or tax liabilities. Here, 39,799 Flywire shares were withheld by the issuer for income tax withholding on RSU settlement, per the footnote, and do not represent an open market sale.

AI-generated analysis. How Rhea-AI works. Not financial advice.

Form 4 Insider Transactions: What Each Field Means →

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Accepted by SEC EDGAR 06/03/2026 - 04:28 PM EDT

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Massaro Michael

(Last)

(First)

(Middle)

C/O FLYWIRE CORPORATION

141 TREMONT STREET, SUITE 10

(Street)

BOSTON

MASSACHUSETTS

02111

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Flywire Corp [ FLYW ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Executive Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/01/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Voting Common Stock	06/01/2026		F		39,799⁽¹⁾	D	$16.61	2,726,236	D
Voting Common Stock								192,193	I	See footnote⁽²⁾
Voting Common Stock								307,548	I	See footnote⁽³⁾

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. Represents the number of shares of common stock that have been withheld by the Issuer to satisfy its income tax withholding and remittance obligations in connection with the net settlement of certain time-based restricted stock unit awards and does not represent an open market sale.

2. The shares are held by the M Massaro Trust, of which the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16 or for any other purpose, except to the extent of the Reporting Person's pecuniary interests therein, if any.

3. The shares are held by the Michael P. Massaro 2021 Irrevocable Trust, of which the Reporting Person's spouse is a trustee. The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission that the Reporting Person is the beneficial owner of such shares for purposes of Section 16 or for any other purpose, except to the extent of the Reporting Person's pecuniary interests therein, if any.

	/s/ Michael Massaro	06/03/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR