Ryan Schaffer
About Ryan Schaffer
Ryan Schaffer (age 38) is Expensify’s Chief Financial Officer and a director, roles he has held since 2017; he previously served as Director of Marketing & Strategy from 2013–2017 and holds a B.S. in business from the University of Dayton . During his tenure, Expensify’s total shareholder return (TSR) on a $100 initial investment fell from $20.06 (2022) to $5.61 (2023) and $7.60 (2024), while net income was a loss of $27.0M (2022), $41.5M (2023), and $10.1M (2024) . Schaffer has led board meetings since 2019 and, as CFO, has driven capital allocation actions including initiating buyback programs (2022 and 2025) and deleveraging to debt‑free status in 2024 .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Expensify, Inc. | Chief Financial Officer and Director | 2017–Present | CFO oversight; leads board meetings since 2019 |
| Expensify, Inc. | Director of Marketing & Strategy | 2013–2017 | Drove marketing and strategy prior to CFO role |
| Various companies | Marketing roles | Pre‑2013 (unspecified) | Prior marketing experience (not specified) |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Expensify.org (non‑profit) | Board member | Not specified (active as of 2024) | Governance of affiliated 501(c)(3); community engagement |
Fixed Compensation
| Metric | FY 2021 | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|---|
| Salary ($) | 725,294 | 854,245 | 1,035,779 | 1,064,689 |
| Bonus ($) | 566,516 | 10,505 | — | — |
| Stock Awards ($) | 5,128,747 | 1,755 | 89,736 | 164,395 |
| Option Awards ($) | 174,806 | — | — | — |
| All Other Compensation ($) | 2,957,368 | 8,335 | 7,910 | 7,772 |
| Total ($) | 9,552,731 | 874,840 | 1,133,425 | 1,236,856 |
Notes:
- Expensify uses a peer‑ranking compensation algorithm company‑wide; executive targets can be reviewed/adjusted by the Compensation Committee (which includes executives) . NEOs must contribute at least a combined 30% of target compensation to the 2021 Stock Purchase & Matching Plan and legacy equity programs; 2024 matching rate: 5% (1/20th share matched per share purchased/retained) .
Performance Compensation
- No formal annual cash bonus plan or pre‑set performance metrics; the Board/Compensation Committee retains discretion to award bonuses but none were paid to Schaffer in 2023–2024 .
- Primary equity vehicle is the 2021 Stock Purchase & Matching Plan; in 2023, Schaffer received matching shares and discretionary fully‑vested share grants under this plan (see grants table below) .
- 2021 time‑based RSUs vest over 8 years (service‑based), 12.5% per year in substantially equal quarterly installments; no explicit financial/TSR performance conditions .
| Incentive Element | Metric | Weighting | Target | Actual/Payout | Vesting |
|---|---|---|---|---|---|
| Annual Cash Bonus | None | N/A | N/A | No payout disclosed for 2023–2024 | N/A |
| 2021 RSU Grant | Service (time‑based) | 100% | 8‑year vest | Ongoing vesting; no performance gate | 12.5% annually in quarterly tranches |
| Stock Purchase & Matching Plan | Share purchase/retention | N/A | 5% match in 2023–2024 | Matching and discretionary shares granted; details below | Fully vested at issuance |
2023 grants to Schaffer (selected):
- Matching shares under plan: 244 (3/15/23), 341 (6/15/23), 536 (9/15/23), 948 (12/15/23) .
- Discretionary fully‑vested shares: 2,308 (7/10/23), 5,242 (9/12/23), 16,737 (11/20/23) .
Equity Ownership & Alignment
Beneficial ownership (as of April 22, 2025)
| Item | Detail |
|---|---|
| Class A shares | 442,936 (less than 1% of Class A) |
| LT10 shares | 498,090 (11.8% of LT10) |
| LT50 shares | 54,915 (less than 1% of LT50) |
| % of total voting power | 1.6% |
| Options exercisable within 60 days | 286,043 shares (various grants) |
Outstanding equity awards (as of Dec 31, 2024)
| Instrument | Amount | Market Value | Vesting / Terms |
|---|---|---|---|
| Unvested RSUs | 149,054 units | $499,331 (at $3.35 on 12/31/24) | 2021 grant; 12.5% annually in quarterly installments over 8 years |
Alignment policies and practices
- Mandatory equity participation: NEOs must allocate at least 30% of target compensation to equity programs (with a 5% matching rate in 2024) .
- Hedging prohibited for directors, officers, employees .
- Limited pledging permitted (up to 25% of holdings; excluding margin loans) with pre‑approved guidelines; the 2025 proxy notes David Barrett’s pledged shares but provides no such disclosure for Schaffer .
Employment Terms
| Term | Summary |
|---|---|
| Employment status | At‑will; employment agreements set terms for NEOs |
| Severance | None upon involuntary termination under current agreements |
| Change‑of‑control | Under the 2021 Incentive Award Plan, if awards are not assumed/substituted in a CIC, unvested equity vests immediately prior to close (single‑trigger if not assumed). As of 12/31/2023, estimated acceleration value for Schaffer was $1,399,198 (if not assumed) |
| Clawback | Adopted Nov 1, 2023; recovery of erroneously awarded incentive compensation for 3 years preceding a restatement, per Nasdaq Rule 10D‑1 |
| Non‑compete / non‑solicit | Not disclosed in proxies reviewed |
| Perquisites | None provided to NEOs in 2023–2024 |
Board Governance
- Role and independence: Schaffer is a management director and not independent; Expensify is a Nasdaq “controlled company” utilizing exemptions from majority‑independent board and independent compensation committee requirements .
- Committees: Member of the Executive Committee (which wields broad board authority while the Voting Trust controls >50% of votes) and the Compensation Committee; not on the Audit Committee (which is fully independent) .
- Compensation Committee interlocks: Executives (CEO Barrett, CFO Schaffer, COO Muralidharan) participate in compensation deliberations, excluding matters about themselves when outside the algorithm .
- Board process: Board, Compensation, and Audit each held four meetings in FY2024; all directors met ≥75% attendance; executive sessions of independent directors held at least annually; no chair or lead independent director designated .
- Director pay: Employee‑directors receive no additional compensation for board service . Non‑employee program: $30,000 annual cash retainer (+$10,000 Audit member; +$20,000 Audit chair) and ~$125,000 annual RSU grant; retainer can be taken in RSUs; RSUs vest on the next annual meeting or first anniversary .
Performance & Track Record
- Capital allocation: Announced $50M buyback authorization (2022) and renewed $50M program (2025); CFO commentary emphasized free cash flow and share repurchases as a return‑of‑capital lever .
- Balance sheet: Company repaid all debt in 2024 (paid off revolver and HQ mortgage) and repurchased 645,938 Class A shares from the founder; CFO signed the purchase agreement and highlighted improved cash flow following cost reductions .
- Results context: TSR on $100 initial investment ended 2024 at $7.60, with net loss of $10.1M in 2024 (vs. $41.5M in 2023), indicating some improvement in losses amid a multi‑year stock decline since the 2021 listing .
Compensation Structure Analysis
- Pay mix: Heavy fixed cash plus time‑based equity; no formulaic performance cash bonus and no disclosed PSU metrics → limited pay‑for‑performance linkage .
- Equity design: Long eight‑year RSU vesting schedule promotes retention; additional fully‑vested discretionary and matching shares under the stock purchase plan can offset some performance risk for executives .
- Governance risk: Compensation Committee includes executives; controlled company structure reduces independent oversight on pay .
- Historical red flag: Company recognized incremental fair value from option repricing in 2021 (IPO year), though no such actions are disclosed for 2023–2024 .
Risk Indicators & Red Flags
- Controlled company with concentrated voting (Voting Trust ~84.3% of voting power as of 4/22/2025) .
- Executive participation in Compensation Committee deliberations (including CFO) .
- Section 16(a) compliance: Multiple late Form 4 filings, including for Schaffer, in 2023–2024 disclosures .
- Pledging policy allows limited pledging; CEO Barrett had shares pledged (no similar disclosure for Schaffer) .
- Single‑trigger equity acceleration if awards are not assumed in a change‑of‑control may misalign with best practices .
Equity Ownership & Director Service Details
| Item | Detail |
|---|---|
| Years on Expensify Board | Since 2017 |
| Committee roles | Executive Committee member; Compensation Committee member; not on Audit |
| Independence | Not independent (management director); company avails “controlled company” exemptions |
| Attendance | ≥75% board/committee attendance in FY2024 for all directors |
| Director compensation | None for employee‑directors |
Say‑on‑Pay & Shareholder Feedback
- Frequency: Annual say‑on‑pay vote affirmed by the Board; next vote expected at 2026 annual meeting .
- Approval percentages: Not disclosed in the reviewed proxies.
Compensation Peer Group
- Process: Semler Brossy engaged in 2023 to provide market data; the committee does not benchmark to a specific percentile; no new consultant retained in 2024 and no executive pay changes made in 2024 .
Investment Implications
- Pay‑for‑performance alignment is weak (no formulaic bonus/PSU metrics), and executive involvement in compensation decisions plus controlled‑company status heighten governance risk; these factors can pressure say‑on‑pay support and introduce agency concerns .
- Retention risk is moderated by long‑duration RSU vesting and a mandatory equity participation policy, though absence of severance protection lowers management’s downside cushion in a transition scenario .
- Ownership alignment is decent (ongoing equity accumulation; no hedging; limited pledging), but Schaffer’s voting power is relatively small (1.6%) within a highly concentrated voting structure dominated by the Voting Trust .
- Operationally, debt elimination and sustained buybacks signal management’s confidence in cash generation and share undervaluation; however, multi‑year TSR remains deeply negative, and continued fundamental improvement is needed to translate cost cuts and capital returns into shareholder value .