EXFY Form 4: CFO Ryan Schaffer Ups Stake, Minor Tax Sale

Rhea-AI Filing Summary

Expensify (EXFY) – Form 4 insider activity

CFO & Director Ryan Schaffer reported several equity transactions executed 13-17 June 2025.

• Open-market purchase: 8,428 Class A shares bought at $2.29 through the 2021 Stock Purchase & Matching Plan (SPMP).
• Matched grant: 5,382 additional shares received at $0 cost under the SPMP.
• RSU conversion: 3,923 vested RSUs settled into Class A shares.
• Tax-related sale: 1,883 shares sold at a weighted-average $2.28; proceeds used solely to cover withholding taxes.

Net effect: Schaffer’s direct Class A holding rose by 7,422 shares to 171,998 (+4.5%). He also retains 66,682 vested RSUs and 58,838 LT50 shares (indirect via Voting Trust) that are convertible 1-for-1 into Class A stock.

The discretionary purchases at market price—combined with the absence of material dispositions—suggest modest insider confidence. The filing contains no operational or earnings data; its relevance is limited to ownership changes.

Positive

• CFO increased direct ownership by 7,422 shares, a 4.5% rise that may indicate confidence in EXFY’s valuation.
• Purchases executed at market price ($2.29) signal discretionary commitment rather than low-cost option exercise.
• Retention of 66,682 RSUs and 58,838 LT50 shares continues to align long-term incentives with shareholder value.

Negative

• 1,883 shares sold to cover taxes slightly offsets the positive signal, though not discretionary.
• The filing provides no operational or financial performance data, limiting its standalone investment relevance.

Insights

Securities Analyst

TL;DR: CFO net-bought 7.4k shares; small sale was tax-driven—signal marginally bullish.

Insider buying from a C-suite officer typically carries signalling value. Schaffer paid $2.29 in cash for 8.4k shares and accepted 5.4k matched shares, implying a personal outlay of roughly $19k. The sale of 1.9k shares at $2.28 was non-discretionary, leaving a net increase of 7.4k shares (+4.5%). Ownership now stands near 172k shares plus unexercised equity awards exceeding 125k shares, strengthening alignment with public shareholders. While the dollar size is modest, the direction is positive and occurs near multi-year share-price lows, which I view as a constructive but limited catalyst.

Corporate Governance Expert

TL;DR: Routine equity plan activity; governance risk unchanged—overall neutral impact.

The Form 4 reflects normal programmatic transactions under Expensify’s SPMP and scheduled RSU vesting. The matched-share feature and tax-sale mechanics are standard. The LT50 shares remain locked in a Voting Trust, maintaining founder control structures; this filing neither increases nor diminishes that dual-class dynamic. Therefore, while insider alignment inches higher, board-level governance characteristics are effectively unchanged.

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^*

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)
06/13/2025

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	06/13/2025		A		8,428(1)	A	$2.29	164,576	D
Class A Common Stock	06/13/2025		A		5,382(2)	A	$0	169,958	D
Class A Common Stock	06/15/2025		M		3,923	A	(3)	173,881	D
Class A Common Stock	06/17/2025		S		1,883(4)	D	$2.28(5)	171,998	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)	06/15/2025		M			3,923	(6)	12/15/2029	Class A Common Stock	3,923	$0	66,682	D
Restricted Stock Units	(7)	06/15/2025		M			3,923	(6)	12/15/2029	LT50 Common Stock	3,923	$0	66,682	D
LT50 Common Stock	(7)(8)	06/15/2025		M		3,923		(8)	(8)	Class A Common Stock	3,923	$0	58,838	I	See note(9)

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 awarded 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 $2.23 to $2.32, 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. The RSUs vest 12.5% on September 15, 2022 and 1/32nd each quarter thereafter, on December 15th, March 15th, June 15th, and September 15th.

7. 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.

8. 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.

9. 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	06/18/2025
	** 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

How many EXFY shares did CFO Ryan Schaffer buy on 13 June 2025?

He purchased 8,428 Class A shares at $2.29 each under the SPMP.

What was the net change in Schaffer’s direct EXFY ownership after the transactions?

His holding increased by 7,422 shares, rising from 164,576 to 171,998.

Why were 1,883 EXFY shares sold on 17 June 2025?

The shares were sold at a weighted $2.28 solely to cover tax withholding for matched-share grants.

What are LT50 shares mentioned in the Form 4?

LT50 Common Stock converts 1-for-1 into Class A shares after notice requirements; Schaffer holds 58,838 indirectly via a Voting Trust.

Does this Form 4 include any earnings or revenue information for Expensify?

No. The filing only discloses insider equity transactions; it contains no operating or financial results.