Expensify (EXFY) Insider Activity: RSU Settlements and Small Sales to Cover Taxes

Rhea-AI Filing Summary

Insider transactions by Expensify, Inc. (EXFY) show CEO and director David Barrett acquiring and settling equity awards and selling shares to cover taxes in mid-September 2025. On 09/15/2025 he was granted 6,507 matched Class A shares and 14,463 restricted stock units (RSUs) that settled into Class A and LT50 shares; the RSUs vest on a schedule through 12/15/2029. Sales occurred on 09/16/2025 (2,396 shares at a weighted average $1.90) and 09/18/2025 (10,262 shares at a weighted average $1.95) to cover tax obligations. Following these transactions he directly owned 218,661 Class A shares and indirectly held 1,468,480 shares via Barrett Trust LLC, with additional convertible LT50 holdings and 3,583,249 shares noted as indirectly owned.

Positive

• Retention-aligned compensation: Grants include matched shares and RSUs that encourage long-term alignment through multi-year vesting schedules.
• Significant indirect ownership: Reporting Person retains substantial control via Barrett Trust LLC and LT50 convertible holdings, indicating aligned insider interest.

Negative

• Minor open-market sales: 12,658 shares sold at weighted averages of $1.90 and $1.95 could modestly increase free float in the short term.
• Complex ownership structure: LT50 conversion restrictions and Voting Trust deposits complicate clarity on near-term voting and liquidity of those shares.

Insights

Corporate Governance Expert

TL;DR: Insider exercised and settled equity awards while selling a small portion to cover taxes; substantial indirect holdings remain.

The filings indicate routine executive equity activity: matched shares under the SPMP and RSU settlements. Sales on 09/16 and 09/18 were executed to satisfy tax withholding, reported at weighted average prices of $1.90 and $1.95 respectively. Ownership remains concentrated: the reporting person retains direct and significant indirect control through Barrett Trust LLC and LT50 convertible shares. From a governance perspective, these transactions do not reflect a reduction of control but show standard post-vesting tax-related sales.

Securities Analyst

TL;DR: Transactions are non-dilutive settlements and small open-market sales; material ownership concentration persists.

The 6,507 matched shares and 14,463 RSU settlements are equity compensation events rather than capital-raising. Reported sales totaling 12,658 shares at sub-$2 prices are minor relative to the large indirect positions reported (over one million shares via trust and millions of LT50-convertible shares). These sales are unlikely to be value-driving for the equity but are relevant for short-term float and tax disclosure. The presence of LT50 convertible instruments and voting trust deposits adds complexity to actual voting and conversion timing.

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

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

1. Name and Address of Reporting Person^*

Barrett David Michael

(Last) (First) (Middle)

C/O EXPENSIFY, INC.

401 SW 5TH AVE

(Street)

PORTLAND OR 97204

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Expensify, Inc. [ EXFY ]

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

3. Date of Earliest Transaction (Month/Day/Year)
09/15/2025

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

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

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

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
Class A Common Stock	09/15/2025		A		6,507(1)	A	$0	206,594	D
Class A Common Stock	09/15/2025		M		14,463	A	(2)	221,057	D
Class A Common Stock	09/16/2025		S		2,396(3)	D	$1.9(4)	218,661	D
Class A Common Stock	09/18/2025		S		10,262(5)	D	$1.95(6)	208,399	D
Class A Common Stock								1,468,480	I	See note(7)

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
Restricted Stock Units	(2)	09/15/2025		M			14,463	(8)	12/15/2029	Class A Common Stock	14,463	$0	231,410	D
Restricted Stock Units	(9)	09/15/2025		M			14,463	(8)	12/15/2029	LT50 Common Stock	14,463	$0	231,410	D
LT50 Common Stock	(9)(10)	09/15/2025		M		14,463		(10)	(10)	Class A Common Stock	14,463	$0	231,410	I	See note(11)
LT50 Common Stock	(10)							(10)	(10)	Class A Common Stock	3,583,249		3,583,249	I	See note(7)(11)

Explanation of Responses:

1. Shares granted as matched shares pursuant to the Expensify, Inc. 2021 Stock Purchase and Matching Plan ("SPMP").

2. Each restricted stock unit ("RSU") represents the contingent right to receive one share of Class A common stock. This transaction represents the settlement of vested RSUs in shares of Class A Common Stock.

3. Represents the Reporting Person's pro rata portion of the total shares sold on the transaction date to cover taxes for shares granted as matched shares under the SPMP for certain employees of the Issuer.

4. The price reported in Column 4 is a weighted average price of all shares sold on the transaction date by the Issuer's broker to cover taxes for shares granted as matched shares under the SPMP for certain employees of the Issuer. These shares were sold in multiple transactions at prices ranging from $1.86 to $1.92, 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 shares sold at each separate price within the range set forth in this footnote.

5. Represents the Reporting Person's pro rata portion of the total shares sold on the transaction date to cover taxes upon the vesting of RSUs for certain employees of the Issuer.

6. The price reported in Column 4 is a weighted average price of all shares sold on the transaction date by the Issuer's broker to cover taxes upon the vesting of RSUs for certain employees of the Issuer. These shares were sold in multiple transactions at prices ranging from $1.91 to $2.00, 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 shares sold at each separate price within the range set forth in this footnote.

7. By Barrett Trust LLC, a manager-managed limited liability company. The investment and voting decisions of Barrett Trust LLC are made by its manager, the Reporting Person, and its controlling member is the Barrett Family Trust, for which the Reporting Person serves as trustee.

8. The restricted stock units vest 12.5% on September 15, 2022 and 1/32nd each quarter thereafter, on December 15th, March 15th, June 15th and September 15th.

9. Each RSU represents the contingent right to receive one share of LT50 common stock. This transaction represents the settlement of vested RSUs in shares of LT50 Common Stock.

10. The LT50 Common Stock is convertible into the Issuer's Class A Common Stock on a one-to-one basis only upon, and generally cannot be transferred without, satisfaction of certain notice and other requirements, including a notice period of 50 months. The LT50 Common Stock will automatically convert into shares of the Issuer's Class A Common Stock on a one-to-one basis at such time as all of the then-outstanding shares of LT10 and LT50 Common Stock represent, in the aggregate, less than 2% of all then-outstanding shares of common stock.

11. Deposited into the Expensify Voting Trust (the "Voting Trust"). The Reporting Person retains investment control and dispositive power over the shares deposited into the Voting Trust.

Remarks:

	/s/ Ryan Schaffer, as attorney-in-fact	09/24/2025
	** 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.
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FAQ

What trades did the Expensify (EXFY) CEO report on Form 4?

The CEO reported grants of 6,507 matched Class A shares and 14,463 RSUs on 09/15/2025, and sales of 2,396 shares on 09/16/2025 and 10,262 shares on 09/18/2025 to cover taxes.

How many EXFY shares does David Barrett beneficially own after these transactions?

The report lists 218,661 direct Class A shares and 1,468,480 indirect shares held via Barrett Trust LLC, plus additional convertible and LT50 holdings noted in the filing.

Why were shares sold in the Form 4 for EXFY?

The filing states the shares sold were the Reporting Person’s pro rata portion sold by the issuer’s broker to cover taxes related to matched shares and RSU vesting.

What prices were reported for the EXFY share sales?

The weighted average sale prices reported were approximately $1.90 for the 09/16/2025 sales (range $1.86–$1.92) and $1.95 for the 09/18/2025 sales (range $1.91–$2.00).

Do the LT50 shares convert to Class A shares for EXFY?

Yes; the LT50 Common Stock is convertible on a one-to-one basis into Class A Common Stock but conversion and transfer are subject to notice and timing requirements, including a 50-month notice period as described in the filing.