Expensify insider activity: purchase, RSU settlement and tax-covering sales reported

Rhea-AI Filing Summary

Ryan Schaffer, Chief Financial Officer and Director of Expensify, Inc. (EXFY), reported multiple insider transactions dated September 15–18, 2025. On 09/15/2025 he purchased 9,566 shares under the 2021 Stock Purchase and Matching Plan at $1.94 per share and received 6,098 matched shares at no cost. The filing also shows settlement of 3,922 vested restricted stock units into Class A and LT50 common stock. On 09/16/2025 and 09/18/2025 he sold a combined 4,936 shares to cover taxes at weighted average prices of approximately $1.90 and $1.95, respectively. After the reported transactions the filing shows beneficial ownership in Class A common stock of 185,937 shares, and certain LT50 shares were deposited into the Expensify Voting Trust while the reporting person retains investment and dispositive control.

Positive

• Insider purchase of 9,566 shares under the SPMP at $1.94, indicating personal capital commitment to the company.
• Receipt of 6,098 matched shares at no cost under the SPMP, reflecting participation in the company’s employee alignment program.
• Vested RSUs settled into Class A and LT50 shares, showing realization of long-term compensation rather than immediate large-scale selling.
• Reporting person retains investment and dispositive power for shares deposited into the Expensify Voting Trust, preserving governance control.

Negative

• Sale of 4,936 shares to cover taxes (2,204 on 09/16/2025 and 2,732 on 09/18/2025) reduced Class A holdings and produced realized dispositions.
• Weighted-average sale prices for tax-covering sales were in a narrow low range ($1.86–$2.00 reported ranges), indicating limited upside in those specific transactions.

Insights

Securities Analyst

TL;DR: Routine insider activity showing share purchases, RSU settlement, and tax-covering sales; overall holding remains substantial.

The transactions are consistent with standard compensation and purchase plan mechanics: an open-market purchase under the SPMP, matched-share grants, and settlement of vested RSUs. The subsequent small-volume sales on 09/16 and 09/18 were executed to cover tax obligations and do not appear to be signal-driven dispositions. Reported pricing ranges and weighted averages are disclosed in footnotes, and the reporting person retains investment and dispositive power over shares placed into the Voting Trust. This filing appears operationally routine and provides transparency on insider alignment with shareholders.

Corporate Governance Expert

TL;DR: Compensation-driven equity activity with governance controls; Voting Trust deposit preserves voting arrangements while retaining control.

The settlement of RSUs into LT50 shares and deposit into the Expensify Voting Trust indicates use of long‑term restricted instruments and a mechanism to centralize voting while preserving the reporting person’s investment control. Matched-share mechanics under the SPMP are disclosed clearly, and tax-covering sales are identified with weighted average prices. These are routine governance and compensation actions, disclosed in compliance with Section 16 reporting requirements.

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).

1. Name and Address of Reporting Person^*

Schaffer Ryan

(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 Financial 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		9,566(1)	A	$1.94	180,853	D
Class A Common Stock	09/15/2025		A		6,098(2)	A	$0	186,951	D
Class A Common Stock	09/15/2025		M		3,922	A	(3)	190,873	D
Class A Common Stock	09/16/2025		S		2,204(4)	D	$1.9(5)	188,669	D
Class A Common Stock	09/18/2025		S		2,732(6)	D	$1.95(7)	185,937	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			3,922	(8)	12/15/2029	Class A Common Stock	3,922	$0	62,760	D
Restricted Stock Units	(9)	09/15/2025		M			3,922	(8)	12/15/2029	LT50 Common Stock	3,922	$0	62,760	D
LT50 Common Stock	(9)(10)	09/15/2025		M		3,922		(10)	(10)	Class A Common Stock	3,922	$0	62,760	I	See note(11)

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.

Remarks:

	/s/ Ryan Schaffer	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.
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.

FAQ

What insider transactions did EXFY CFO Ryan Schaffer report on Form 4?

The Form 4 reports a purchase of 9,566 Class A shares at $1.94, receipt of 6,098 matched shares at $0, settlement of 3,922 vested RSUs, and sales of 2,204 and 2,732 shares to cover taxes.

How many shares does Ryan Schaffer beneficially own after the reported transactions (EXFY)?

The filing shows 185,937 Class A common shares beneficially owned following the transactions reflected in the Form 4.

Why were some shares sold by the reporting person on 09/16/2025 and 09/18/2025 (EXFY)?

The filing states those sales represent the reporting person’s pro rata portion of shares sold by the issuer’s broker to cover taxes related to matched shares and vested RSUs.

What are LT50 shares reported in the Form 4 for EXFY?

LT50 common stock is convertible into Class A common stock on a one-to-one basis subject to notice and transfer restrictions including a 50-month notice period; conversion is automatic when LT10 and LT50 aggregate to less than 2% of outstanding common stock.

Were any shares deposited into a voting arrangement in this filing (EXFY)?

Yes, certain LT50 shares were deposited into the Expensify Voting Trust, and the reporting person retains investment and dispositive power over those shares.