Form 4: Expensify CFO Ryan Schaffer Reports Stock Plan Award and Tax-Related Share Sale

Expensify's Chief Financial Officer and Director, Ryan Schaffer, reported the acquisition of shares through a stock plan and a subsequent sale of a portion of those shares to cover tax obligations.

Summary

• Ryan Schaffer, Chief Financial Officer and Director of Expensify, Inc. (EXFY), reported changes in his beneficial ownership of Class A Common Stock.
• On May 29, 2025, Mr. Schaffer acquired 1,973 shares of Class A Common Stock at a price of $0, which were awarded under the Expensify, Inc. 2021 Stock Purchase and Matching Plan ("SPMP").
• On May 30, 2025, Mr. Schaffer disposed of 716 shares of Class A Common Stock at a weighted average price of $2.22 per share.
• The disposition of shares was a pro rata portion of the total shares sold on that date by the Issuer's broker to cover taxes for shares awarded under the SPMP for certain employees of Expensify.
• The sale price of $2.22 represents a weighted average, with individual transactions ranging from $2.17 to $2.26.
• Following these transactions, Mr. Schaffer's direct beneficial ownership of Class A Common Stock stands at 156,148 shares.

Sentiment

Score: 5

Explanation: The filing reports routine insider stock transactions, including an award and a tax-related sale, which are generally neutral in sentiment as they are common occurrences for executives receiving equity compensation.

Positives

• The acquisition of 1,973 shares through the Expensify, Inc. 2021 Stock Purchase and Matching Plan indicates ongoing equity participation and alignment of management interests with shareholders.
• Despite the tax-related sale, there was a net increase of 1,257 shares in the reporting person's beneficial ownership (1,973 acquired 716 disposed).

Negatives

• A portion of the awarded shares (716 shares) was immediately sold, reducing the direct holdings, although this was for tax coverage purposes.

Future Outlook

This Form 4 filing does not contain any forward-looking statements or guidance regarding the company's future performance or outlook.

Industry Context

This filing is a routine insider transaction report and does not provide broader industry context or trends. It reflects an individual executive's equity compensation and tax management related to that compensation within Expensify.

Related Party Transactions

• The acquisition of shares was made under the Expensify, Inc. 2021 Stock Purchase and Matching Plan (SPMP), which is a compensation arrangement between the company and its employees/officers.

Stakeholder Impact

• Shareholders: The filing indicates continued equity alignment of a key executive with the company's performance through stock awards, although a portion was sold for tax purposes. The net increase in holdings could be viewed positively.
• Employees: The transaction relates to the company's Stock Purchase and Matching Plan, which is part of employee compensation.

Next Steps

• The Reporting Person undertakes to provide full information regarding the number of shares sold at each separate price within the reported range upon request from the Issuer, any security holder, or the SEC staff.

Key Dates

Keywords

Expensify, EXFY, Ryan Schaffer, Form 4, Insider Transaction, Stock Award, Tax Sale, Beneficial Ownership, CFO, Director, Equity Compensation