Were Flywire (FLYW) CEO share sales made under a Rule 10b5-1 plan?

Yes. The filing states the 50,000 shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan. Such plans pre-schedule trades, helping separate routine diversification or liquidity needs from discretionary timing decisions by the insider.

Flywire (NASDAQ: FLYW) CEO sells 50,000 shares in pre-set trading plan

Filing Impact

(Very High)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Flywire Corp Chief Executive Officer Michael Massaro reported an open-market sale of 50,000 shares of Voting Common Stock on June 15, 2026. The shares were sold at a weighted average price of $15.2588 per share under a previously adopted Rule 10b5-1 trading plan.

After this transaction, Massaro directly holds 2,678,051 shares of Voting Common Stock. Additional shares are held indirectly through the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust, where his spouse serves as trustee and he disclaims beneficial ownership except for any pecuniary interests.

Insider Trade Summary 10b5-1

Net Seller: 50,000 shares ($762,940)

Net Sell 3 txns

Insider Massaro Michael

Role Chief Executive Officer

Sold 50,000 shs ($763K)

Type	Security	Shares	Price	Value
Sale	Voting Common Stock	50,000	$15.2588	$763K
holding	Voting Common Stock	--	--	--
holding	Voting Common Stock	--	--	--

Holdings After Transaction: Voting Common Stock — 2,678,051 shares (Direct, null); Voting Common Stock — 192,193 shares (Indirect, See footnote)

Footnotes (1)

Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.01 to $15.49, inclusive. The Reporting Person has provided to the Issuer, and undertakes to provide to the staff of the Securities and Exchange Commission or any security holder of the Issuer, upon request, full information regarding the number of shares sold at each separate price within the range. Adjusted to reflect 1,815 shares acquired under the Issuer's Employee Stock Purchase Plan. 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. 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

Shares sold: 50,000 shares Weighted average sale price: $15.2588 per share Direct holdings after sale: 2,678,051 shares +3 more

6 metrics

Shares sold 50,000 shares Open-market sale of Voting Common Stock on June 15, 2026

Weighted average sale price $15.2588 per share Sale prices ranged from $15.01 to $15.49

Direct holdings after sale 2,678,051 shares Voting Common Stock held directly by CEO after transaction

Indirect trust holding (M Massaro Trust) 307,548 shares Held by M Massaro Trust; CEO disclaims beneficial ownership except pecuniary interests

Indirect trust holding (2021 Irrevocable Trust) 192,193 shares Held by Michael P. Massaro 2021 Irrevocable Trust; CEO disclaims beneficial ownership except pecuniary interests

ESPP acquisition adjustment 1,815 shares Acquired under Flywire’s Employee Stock Purchase Plan and reflected in holdings

Key Terms

Rule 10b5-1 trading plan, weighted average price, Employee Stock Purchase Plan, pecuniary interests, +1 more

5 terms

Rule 10b5-1 trading plan regulatory

"Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan."

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

weighted average price financial

"The price reported in Column 4 is a weighted average price."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

Employee Stock Purchase Plan financial

"Adjusted to reflect 1,815 shares acquired under the Issuer's Employee Stock Purchase Plan."

An employee stock purchase plan is a company program that lets workers buy shares through small payroll deductions, often at a discount to the market price and after a set offering period. Think of it like a workplace savings plan that turns into ownership: it encourages employees to share in the company’s success and can create predictable buying or selling of stock that investors watch because it affects supply, demand and employee incentives.

pecuniary interests financial

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

disclaims beneficial ownership regulatory

"The Reporting Person disclaims beneficial ownership of these shares and this report shall not be deemed an admission"

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Form 4 Insider Transactions: What Each Field Means →

06/17/2026 - 04:14 PM

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)
06/15/2026

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	06/15/2026		S⁽¹⁾		50,000	D	$15.2588⁽²⁾	2,678,051⁽³⁾	D
Voting Common Stock								192,193	I	See footnote⁽⁴⁾
Voting Common Stock								307,548	I	See footnote⁽⁵⁾

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. Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.01 to $15.49, inclusive. The Reporting Person has provided to the Issuer, and undertakes to provide to the staff of the Securities and Exchange Commission or any security holder of the Issuer, upon request, full information regarding the number of shares sold at each separate price within the range.

3. Adjusted to reflect 1,815 shares acquired under the Issuer's Employee Stock Purchase Plan.

4. 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.

5. 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	06/17/2026
	** 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

FAQ

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

Michael Massaro reported selling 50,000 shares of Flywire Voting Common Stock. The sale occurred on June 15, 2026, as an open-market transaction executed under a previously adopted Rule 10b5-1 trading plan, indicating it was pre-scheduled rather than a discretionary trade.

At what price did the Flywire (FLYW) CEO sell the 50,000 shares?

The 50,000 shares were sold at a weighted average price of $15.2588 per share. The filing notes multiple trades between $15.01 and $15.49, and detailed trade-level pricing is available from the issuer or the CEO upon request.

How many Flywire (FLYW) shares does the CEO hold after this sale?

Following the reported sale, Michael Massaro directly holds 2,678,051 shares of Flywire Voting Common Stock. This figure reflects an adjustment for 1,815 shares acquired under the company’s Employee Stock Purchase Plan, as noted in the filing footnotes.

What indirect Flywire (FLYW) holdings are reported for Michael Massaro?

The filing shows indirect holdings through the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust. Both are overseen by his spouse as trustee, and Massaro disclaims beneficial ownership except for any pecuniary interests in those trust-held shares.

How is the Flywire (FLYW) CEO’s sale characterized in the Form 4?

The sale is coded as an open-market or private sale of non-derivative Voting Common Stock. There are no derivative exercises reported, and the transaction is presented alongside updated direct and indirect share balances, giving a snapshot of the CEO’s overall equity position.