Expensify insider activity: purchases, RSU settlements and tax-covering sales by director

Rhea-AI Filing Summary

Insider transactions by Director Jason Fahr Mills at Expensify, Inc. (EXFY) On 09/15/2025 the reporting person acquired 42,947 shares of Class A common stock purchased under the 2021 Stock Purchase and Matching Plan at a weighted average price of $1.94 and received 20,006 matched shares at no cost. The same date shows settlement of 3,821 vested restricted stock units into Class A shares. Subsequent broker-assisted sales on 09/16/2025 and 09/18/2025 disposed of 4,921 and 1,812 shares at weighted average prices reported as $1.90 and $1.95, respectively. After these transactions the reporting person beneficially owned 426,573 shares of Class A common stock directly and retains indirect holdings through LT50 shares deposited in the company Voting Trust.

Positive

• Acquisition of 42,947 shares under the 2021 Stock Purchase and Matching Plan at a weighted average price of $1.94
• Settlement of 3,821 vested RSUs into Class A common stock, increasing direct ownership
• Matched grant of 20,006 shares received at no cost under the SPMP

Negative

• Sales of 6,733 shares in aggregate (4,921 and 1,812) on 09/16/2025 and 09/18/2025, reducing direct holdings to 426,573 shares
• Significant holdings are in LT50 shares with long conversion/transfer restrictions and deposited into a Voting Trust, limiting immediate liquidity of those shares

Insights

Financial Analyst

TL;DR: Director acquired company stock under the employee purchase plan, settled vested RSUs, and sold small portions to cover taxes.

The Form 4 discloses purchases under the issuer's 2021 Stock Purchase and Matching Plan and the settlement of vested restricted stock units, increasing direct holdings. Modest open-market sales occurred on two dates at approximately $1.90–$1.95, noted as broker sales to cover tax obligations for matched shares and RSU vesting. The filing also shows substantial indirect holdings via LT50 shares held in the Voting Trust with conversion and transfer restrictions, and the reporter retains investment and dispositive power over those trust-deposited shares.

Corporate Governance Specialist

TL;DR: Transactions are routine insider activity tied to compensation programs and Voting Trust arrangements, not an extraordinary governance event.

The entry documents routine equity compensation mechanics: matched share grants, RSU settlements, and tax-covering share sales. Importantly, LT50 Common Stock holdings are subject to long notice and transfer conditions and are deposited into the Expensify Voting Trust while the reporting person retains control, which is material to voting power analysis but explicitly described and not a change in governance structure within this filing.

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^*

Mills Jason Fahr

(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
	Officer (give title below)		Other (specify below)

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		42,947(1)	A	$1.94	409,479	D
Class A Common Stock	09/15/2025		A		20,006(2)	A	$0	429,485	D
Class A Common Stock	09/15/2025		M		3,821	A	(3)	433,306	D
Class A Common Stock	09/16/2025		S		4,921(4)	D	$1.9(5)	428,385	D
Class A Common Stock	09/18/2025		S		1,812(6)	D	$1.95(7)	426,573	D

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	(3)	09/15/2025		M			3,821	(8)	12/15/2029	Class A Common Stock	3,821	$0	61,140	D
Restricted Stock Units	(9)	09/15/2025		M			3,821	(8)	12/15/2029	LT50 Common Stock	3,821	$0	61,140	D
LT50 Common Stock	(9)(10)	09/15/2025		M		3,821		(10)	(10)	Class A Common Stock	3,821	$0	45,855	I	See note(11)
LT50 Common Stock	(10)							(10)	(10)	Class A Common Stock	534,925		534,925	I	See note(11)(12)

Explanation of Responses:

1. Shares purchased pursuant to the Expensify, Inc. 2021 Stock Purchase and Matching Plan ("SPMP").

2. Shares granted as matched shares pursuant to the SPMP.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

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.

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

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 insider transactions did Jason Fahr Mills report for EXFY on September 15–18, 2025?

The Form 4 shows a purchase of 42,947 Class A shares at a weighted average price of $1.94, receipt of 20,006 matched shares at $0, settlement of 3,821 vested RSUs, and sales of 4,921 and 1,812 shares on 09/16/2025 and 09/18/2025 at weighted average prices of $1.90 and $1.95 respectively.

Why were some shares sold by the reporting person according to the Form 4?

The filing states the shares sold on the sale dates represent the reporting person’s pro rata portion of shares sold by the issuer’s broker to cover taxes for matched shares and upon RSU vesting.

How many Class A shares does the reporting person beneficially own after these transactions?

After the reported transactions the reporting person beneficially owned 426,573 Class A common shares directly, with additional indirect holdings through convertible LT50 shares held in the Voting Trust.

What are LT50 shares and do they affect voting or transferability?

LT50 Common Stock converts one-for-one into Class A shares only upon certain conditions and generally cannot be transferred without satisfying a ~50-month notice and other requirements; many LT50 shares disclosed are deposited into the Expensify Voting Trust while the reporting person retains investment and dispositive power.

Who signed the Form 4 and when was it filed?

The Form is signed by Ryan Schaffer as attorney-in-fact for the reporting person on 09/24/2025 as indicated on the filing.