Flywire CEO sells 50,000 shares in planned trade

Flywire Corp Chief Executive Officer Michael Massaro reported open-market sales of 50,000 shares of Voting Common Stock.

Rhea-AI Filing Summary

Flywire Corp Chief Executive Officer Michael Massaro reported open-market sales of 50,000 shares of Voting Common Stock. The transactions occurred on May 6, 2026 at weighted average prices of $16.6229 and $15.6543 per share, as part of two separate sale entries. The filing states these shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan. After the sales, Massaro directly holds 2,766,035 shares of Voting Common Stock. Indirect holdings reported in the filing are held by the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust, for which Massaro disclaims beneficial ownership except to the extent of any pecuniary interest.

Insider Trade Summary 10b5-1

Net Seller: 50,000 shares

Net Sell 4 txns

Insider Massaro Michael

Role Chief Executive Officer

Sold 50,000 shs ($820K)

Type	Security	Shares	Price	Value
Sale	Voting Common Stock	11,830	$15.6543	$185K
Sale	Voting Common Stock	38,170	$16.6229	$634K
holding	Voting Common Stock	--	--	--
holding	Voting Common Stock	--	--	--

Holdings After Transaction: Voting Common Stock — 2,766,035 shares (Direct); Voting Common Stock — 499,741 shares (Indirect, See footnote)

Footnotes (5)

1. F1. Shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan.
2. F2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.085 to $16.00, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of securities sold at each separate price within the ranges set forth in this footnote to this Form 4.
3. F3. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.15 to $16.905, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of securities sold at each separate price within the ranges set forth in this footnote to this Form 4.
4. F4. 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. F5. 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 Sale price tranche 1: $16.6229 per share Sale price tranche 2: $15.6543 per share +5 more

8 metrics

Shares sold 50,000 shares Open-market sales of Voting Common Stock on May 6, 2026

Sale price tranche 1 $16.6229 per share Weighted average price for 38,170 shares sold

Sale price tranche 2 $15.6543 per share Weighted average price for 11,830 shares sold

Direct holdings after sale 2,804,205 shares Voting Common Stock held directly following reported transactions

M Massaro Trust holdings 307,548 shares Voting Common Stock held indirectly by M Massaro Trust

2021 Irrevocable Trust holdings 192,193 shares Voting Common Stock held indirectly by Michael P. Massaro 2021 Irrevocable Trust

Price range tranche 1 $15.085–$16.00 Range of prices for trades averaged to $15.6543

Price range tranche 2 $16.15–$16.905 Range of prices for trades averaged to $16.6229

Key Terms

Rule 10b5-1 trading plan, weighted average price, Voting Common Stock, pecuniary interests, +2 more

6 terms

Rule 10b5-1 trading plan financial

"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.

Voting Common Stock financial

"security_title: Voting Common Stock"

pecuniary interests financial

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

Section 16 regulatory

"for purposes of Section 16 or for any other purpose"

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.

Irrevocable Trust financial

"The shares are held by the Michael P. Massaro 2021 Irrevocable Trust"

An irrevocable trust is a legal arrangement where an owner transfers assets into a separate entity managed by a trustee and gives up the power to modify or reclaim those assets. For investors it matters because putting stock or other holdings into such a trust can change who controls and benefits from the assets, affect taxes and creditor protection, and influence how easy it is to sell or value those holdings—like placing valuables in a locked safe overseen by someone else.

FAQ

How many Flywire (FLYW) shares did CEO Michael Massaro sell in this Form 4?

Michael Massaro sold 50,000 shares of Flywire Voting Common Stock. The Form 4 shows two open-market sale transactions totaling 50,000 shares on May 6, 2026, with all sales executed at weighted average prices disclosed in the filing.

At what prices were the Flywire (FLYW) shares sold by the CEO?

The reported weighted average sale prices were $16.6229 and $15.6543 per share. Each price reflects multiple transactions within stated ranges, with one tranche between $16.15 and $16.905, and another between $15.085 and $16.00, as described in the footnotes.

How many Flywire (FLYW) shares does Michael Massaro hold after these transactions?

After the reported sales, Michael Massaro directly holds 2,804,205 shares. The Form 4 also reports additional Voting Common Stock held indirectly through two family trusts, for which he disclaims beneficial ownership except for any pecuniary interests.

What does the Form 4 say about the Rule 10b5-1 trading plan for Flywire (FLYW)?

The filing states the shares were sold pursuant to a previously adopted Rule 10b5-1 trading plan. This disclosure appears in a footnote explaining that the reported sales followed the terms of that established plan.

How are the trust holdings related to Michael Massaro reported for Flywire (FLYW)?

The Form 4 shows shares held by the M Massaro Trust and the Michael P. Massaro 2021 Irrevocable Trust. Each footnote explains his spouse is a trustee and that he disclaims beneficial ownership except for any pecuniary interests.

Were the Flywire (FLYW) share sales by the CEO open-market transactions?

Yes, the Form 4 describes the transactions as sales in the open market or private transactions. The transaction code "S" and its description indicate these were sale transactions rather than option exercises, gifts, or tax withholdings.

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

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Accepted by SEC EDGAR 05/08/2026 - 04:27 PM Learn about SEC filing dates

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).

X

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)
05/06/2026

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)
			Code	V	Amount	(A) or (D)	Price
Voting Common Stock	05/06/2026		S(1)		11,830	D	$15.6543(2)	2,804,205	D
Voting Common Stock	05/06/2026		S(1)		38,170	D	$16.6229(3)	2,766,035	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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

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 $15.085 to $16.00, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of securities sold at each separate price within the ranges set forth in this footnote to this Form 4.

3. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.15 to $16.905, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of securities sold at each separate price within the ranges set forth in this footnote to this Form 4.

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	05/08/2026
	** 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)