Robert Orgel
FlywireAbout Robert Orgel
Robert Orgel is President and Chief Operating Officer of Flywire, serving since November 2019; age 56. He leads business operations, legal, compliance, and corporate strategy, and previously helped launch and scale Apple Pay’s global expansion and the Apple Card. He holds B.A. and M.A. degrees in International Relations from Stanford University and a J.D. from Harvard Law School . Company performance in 2024: total payment volume $29.7B (+23.6% YoY), revenue $492.1M (+22% YoY), Adjusted EBITDA $77.9M; cumulative TSR since IPO measured as $86 on a $100 initial investment, while the S&P 500 Information Technology Sector was $190 over the same window .
Past Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Apple Inc. | Part of leadership team for Apple Pay; launch of Apple Card | 2010–2019 | Developed, launched, and grew Apple Pay globally; launched Apple Card |
| Quattro Wireless, Inc. | Chief Operating Officer | 2008–2010 | Mobile ad-tech; acquired by Apple in 2010 |
| m-Qube, Inc. | Leadership role | Not disclosed | Carrier billing/payment platform; acquired by VeriSign |
| edocs, Inc. | Leadership role | Not disclosed | E-billing/payment solution; acquired by Siebel (later Oracle) |
External Roles
- Not disclosed in the proxy for Mr. Orgel .
Fixed Compensation
| Component | 2024 Amount |
|---|---|
| Base salary | $350,000 |
| Target annual bonus | $225,000 |
| Actual bonus paid (for 2024, paid Mar-2025) | $120,888 (53.7% of target) |
Multi-year summary (total compensation):
| Year | Salary ($) | Stock Awards ($) | Non-Equity Incentive ($) | All Other ($) | Total ($) |
|---|---|---|---|---|---|
| 2022 | 350,000 | 3,192,061 | 195,750 | 10,326 | 3,748,137 |
| 2023 | 350,000 | 4,024,716 | 293,000 | 8,799 | 4,676,515 |
| 2024 | 350,000 | 5,402,978 | 120,888 | 7,748 | 5,881,614 |
Performance Compensation
Annual Incentive Plan (AIP) – 2024
- Structure (corporate-only metrics for NEOs): 50% Revenue Less Ancillary Services; 50% Adjusted EBITDA; max payout 150% of target .
- Outcome: Revenue Less Ancillary Services below threshold (0% factor); Adjusted EBITDA at 107.5% factor; total payout 53.7% of target; Orgel paid $120,888 .
| Metric | Weight | Threshold (50% payout) | Target (100%) | Max (150%) | Actual | Payout Factor |
|---|---|---|---|---|---|---|
| Revenue Less Ancillary Services | 50% | $496.0M | $519.0M | $545.0M | $474.2M adjusted basis used for AIP; for disclosure: $474.2M | 0% |
| Adjusted EBITDA | 50% | $70.5M | $76.1M | $87.5M | $77.9M | 107.5% |
Equity awards (time-based RSUs)
- 2024 grant: RSUs with target grant value $4,650,000; 198,129 shares; vesting 25% after 1 year (Mar 1, 2025), then quarterly over 3 years, subject to continued service .
- Compensation mix emphasizes equity; majority of target direct comp in RSUs; no options granted in 2024 .
| Grant date | Type | Shares | Grant-date fair value ($) | Vesting schedule |
|---|---|---|---|---|
| Mar 2, 2024 | RSU | 198,129 | 5,402,978 | 25% on Mar 1, 2025; remaining quarterly over 3 years |
Outstanding equity and vesting detail (as of Dec 31, 2024)
- Unvested RSUs and their proxy-calculated values at $20.62/share:
- 39,382 RSUs ($1,603,473) – 2022 grant; 25% vested Mar 4, 2023; remaining quarterly over 36 months .
- 84,411 RSUs ($3,299,118) – 2023 grant; 25% vested Mar 1, 2024; remaining quarterly over 36 months .
- 198,129 RSUs ($7,028,678) – 2024 grant; 25% vests Mar 1, 2025; remaining quarterly over 36 months .
- Options outstanding:
- 384,452 options exercisable @ $3.30; exp. 10/31/2029 .
- 225,288 options exercisable @ $3.95; and 9,375 unexercisable @ $3.95; exp. 1/20/2031 (201/2021 grant schedule: 25% on 1/21/2022, remainder monthly over 36 months) .
- 2024 realizations: 25,337 options exercised ($320,513 realized); 97,158 RSUs vested ($2,265,759) .
| Instrument | Exercise/Grant Price | Expiration/First Vest | Exercisable | Unexercisable | Notes |
|---|---|---|---|---|---|
| Stock options | $3.30 | 10/31/2029 | 384,452 | — | Legacy option grant |
| Stock options | $3.95 | 1/20/2031 | 225,288 | 9,375 | 25% on 1/21/2022; rest monthly 36 mos |
| RSUs (2022) | — | 25% on 3/4/2023 | — | 39,382 unvested ($1,603,473) | Quarterly vest thereafter |
| RSUs (2023) | — | 25% on 3/1/2024 | — | 84,411 unvested ($3,299,118) | Quarterly vest thereafter |
| RSUs (2024) | — | 25% on 3/1/2025 | — | 198,129 unvested ($7,028,678) | Quarterly vest thereafter |
AIP program design and governance
- Metrics and weights disclosed; no individual modifiers for NEOs in 2024; max capped at 150% .
- Compensation committee uses peer group (e.g., Asana, AvidXchange, EVERTEC, Nuvei, Payoneer, Repay) and targets 50th–75th percentile for total compensation with equity-heavy mix .
Equity Ownership & Alignment
- Beneficial ownership: 830,066 shares; <1% of outstanding voting common stock (120,004,210 shares outstanding as of Apr 8, 2025) .
- Stock ownership guidelines: executives must hold 2x base salary; compliance evaluated at year-end; each executive officer satisfied guidelines as of 2024 year-end .
- Hedging/pledging: policy prohibits hedging and short sales; pledging permissible only with prior compliance clearance; Rule 10b5-1 trading plans permitted .
- Clawback: policy for recovery of erroneously awarded incentive-based compensation adopted July 2023, aligned with SEC/Nasdaq listing standards .
| Holder | Shares | % of Class |
|---|---|---|
| Robert Orgel | 830,066 | <1% |
Insider supply/vesting cadence and 2024 activity
- Scheduled RSU vesting cadence: time-based RSUs vest quarterly after first-anniversary tranche, creating periodic supply; 2024 award first vest on Mar 1, 2025, then quarterly for three years .
- 2024 realized activity: 25,337 options exercised; 97,158 RSUs vested, indicating realized equity flows during 2024 .
Employment Terms
Severance and change-in-control (CIC) economics (double-trigger; no single-trigger equity acceleration)
- If terminated without cause or resigns for good reason within the CIC window (3 months pre- to 12 months post-CIC):
- Cash severance: 1x (base salary + target bonus) = $575,000 .
- Equity: full acceleration of time-based equity; option cash-out protection if options are terminated at closing, as applicable; COBRA up to 12 months .
- If terminated without cause or resigns for good reason outside CIC window:
- Cash severance: $487,500 (includes salary continuation period and accrued/unpaid bonus mechanics per agreement) .
- Equity: additional six months of vesting on outstanding equity; COBRA for continuation period (nine months for Orgel) .
- Company states it does not provide single-trigger equity acceleration upon a CIC; design is double-trigger .
| Scenario | Cash Severance | RSU Acceleration | Option Acceleration | Benefit Continuation |
|---|---|---|---|---|
| CIC window: term w/o cause or good reason | $575,000 | $6,638,032 | $156,281 | $29,814 |
| Outside CIC window: term w/o cause or good reason | $487,500 | $1,988,284 | $156,281 | $22,360 |
Other terms and policies
- At-will employment; standard confidentiality/IP assignment agreements .
- No tax gross-ups; ownership guidelines enforced; capped bonus payouts; independent compensation consultant; anti-hedging policy .
Investment Implications
- Pay-for-performance alignment is mixed: 2024 AIP paid 53.7% of target due to revenue metric miss (0% factor) but EBITDA outperformance (107.5%), signaling disciplined bonus mechanics tied to profit resilience .
- Equity-heavy mix (RSUs) plus sizable unvested awards (321k+ RSUs at YE 2024 across 2022–2024 grants) strengthens retention/alignment but creates predictable quarterly vesting supply over 2025–2028; 2024 realized vesting/exercises indicate periodic insider liquidity events .
- Change-in-control protection is double-trigger with full time-based equity acceleration in CIC-related terminations, which reduces executive resistance to strategic transactions; outside CIC, only partial (six months) vesting accrues, moderating severance risk .
- Governance guardrails (clawback, no single-trigger, anti-hedging, ownership guidelines met) reduce red-flag risk; pledging requires preclearance, and Rule 10b5-1 plans are permitted, shaping interpretation of future Form 4 sales patterns .