Michael Massaro
FlywireAbout Michael Massaro
Michael Massaro is Flywire’s Chief Executive Officer and a Director (age 46), serving as CEO since December 2013 after joining Flywire in March 2012; he holds a B.S. in Management Information Systems from Babson College and previously worked in global payments and software at edocs (acquired by Siebel), Carrier IQ, and began his career at PwC’s technical risk services practice . Under his leadership, Pay Versus Performance disclosures show 2024 compensation actually paid of $6.45M alongside cumulative TSR of $86 (vs $190 for the S&P 500 IT sector peer group), net income of $2.9M, and Revenue Less Ancillary Services of $474.2M . Flywire’s 2024 annual incentive metrics were Revenue Less Ancillary Services and Adjusted EBITDA, with actuals of $474.2M and $77.9M respectively; the CEO earned 53.7% of his cash bonus target based on these results .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Flywire | Vice President, Sales & Business Development | Mar 2012–Dec 2013 | Senior commercial leadership prior to CEO appointment |
| Flywire | Chief Executive Officer | Dec 2013–Present | Led growth in payments software; long-tenured founder-like leadership |
| edocs (acquired by Siebel Systems) | Executive experience in global payments/software | Not disclosed | Payments and e-billing domain expertise |
| Carrier IQ | Executive experience in mobile software/hardware | Not disclosed | Mobile technology background |
| PricewaterhouseCoopers LLP | Technical Risk Services | Not disclosed | Early-career risk and controls foundation |
External Roles
No public company directorships or committee roles disclosed for Massaro beyond Flywire’s Board seat .
Fixed Compensation
| Metric | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|
| Base Salary ($) | $450,000 | $450,000 | $450,000 |
| Annual Cash Incentive (2024) | Target ($) | Actual Payout ($) | % of Target |
|---|---|---|---|
| CEO Bonus | $450,000 | $241,776 | 53.7% |
| All Other Compensation (2024) | Amount ($) | Details |
|---|---|---|
| CEO | $11,598 | $1,248 insurance; $10,350 401(k) match |
Performance Compensation
| Metric | Weighting | Threshold (50% payout) | Target (100% payout) | Max (150% payout) | Actual | Payout % | Vesting |
|---|---|---|---|---|---|---|---|
| Revenue Less Ancillary Services | 50% | $496.0M | $519.0M | $545.0M | $474.2M | 0% component | N/A (cash) |
| Adjusted EBITDA | 50% | $70.5M | $76.1M | $87.5M | $77.9M | 107.5% component | N/A (cash) |
| 2024 Long-Term Incentive Grant (RSUs) | Grant Date | Target Grant Value ($) | Shares | Grant Date Fair Value ($) | Vesting Schedule |
|---|---|---|---|---|---|
| CEO RSUs | 3/2/2024 | $8,000,000 | 340,867 | $9,295,443 | 25% on 3/1/2025; remainder in equal quarterly installments over 3 years, subject to continued service |
Notes:
- 2024 LTI program used time-based RSUs (no PSUs) given long-term goal-setting challenges; equity dominates target direct compensation (>80%) to align with stock price performance .
Equity Ownership & Alignment
| Beneficial Ownership (as of 4/8/2025) | Shares | % of Class | Within 60 days: Options Exercisable | Within 60 days: RSUs to Vest |
|---|---|---|---|---|
| Michael Massaro | 2,532,738 | 2.1% | 821,137 | 54,833 |
| Outstanding RSUs (12/31/2024) | Unvested Shares | Market Value ($) |
|---|---|---|
| CEO RSUs (various grants) | 77,763 | $1,603,473 |
| CEO RSUs (various grants) | 159,996 | $3,299,118 |
| CEO RSUs (2024 grant) | 340,867 | $7,028,678 |
| Outstanding Options (12/31/2024) | Exercisable (#) | Unexercisable (#) | Exercise Price ($) | Expiration |
|---|---|---|---|---|
| CEO Option | 88,731 | — | 0.59 | 7/25/2026 |
| CEO Option | 23,598 | — | 0.59 | 7/25/2026 |
| CEO Option | 18,435 | — | 3.28 | 2/27/2029 |
| CEO Option | 302,724 | — | 3.30 | 10/31/2029 |
| CEO Option | 293,750 (exercisable) | 6,250 (unexercisable) | 3.95 | 1/20/2031 |
| CEO Option | 235,000 (exercisable) | 65,000 (unexercisable) | 3.95 | 1/20/2031 |
| 2024 Equity Realization | Shares Acquired on Exercise (#) | Value Realized on Exercise ($) | Shares Acquired on Vesting (#) | Value Realized on Vesting ($) |
|---|---|---|---|---|
| Michael Massaro | 107,538 | $2,092,367 | 187,450 | $4,363,830 |
Alignment Policies:
- CEO stock ownership guideline: 5x base salary; all executive officers were in compliance at end of 2024 .
- Insider Trading Policy prohibits hedging and short sales; pledging is permitted only with prior compliance clearance; Rule 10b5-1 plans are allowed and used by certain officers/directors .
Employment Terms
| Scenario | Cash Severance | Equity Acceleration (Options) | Equity Acceleration (RSUs) | Benefit Continuation | Total |
|---|---|---|---|---|---|
| Termination without Cause / Resignation for Good Reason within Change-in-Control Window | $1,350,000 | $1,187,738 | $11,951,888 | $44,721 | $14,534,346 |
| Termination without Cause / Resignation for Good Reason outside Change-in-Control Window | $900,000 | $604,288 | $3,579,199 | $29,814 | $5,113,300 |
Key terms:
- CoC severance multiple: 1.5x of sum of base salary + annual target bonus (CEO) .
- Outside CoC: salary continuation for 12 months; additional six months of vesting on outstanding equity; COBRA premiums paid for 12 months .
- Double-trigger acceleration: time-based equity vests in full upon qualifying termination in CoC window; cash “make-whole” if unvested options/RSUs are terminated without payment at CoC closing, per specified conditions .
- Definitions of “Cause” and “Good Reason” specified in employment agreements .
Performance & Track Record
| Pay vs Performance (Company-wide) | 2021 | 2022 | 2023 | 2024 |
|---|---|---|---|---|
| PEO Compensation Actually Paid ($) | $40,706,656 | ($4,643,996) | $8,251,940 | $6,452,629 |
| Cumulative TSR – Value of $100 | $159 | $102 | $96 | $86 |
| Peer Group TSR – Value of $100 (S&P 500 IT) | $126 | $89 | $140 | $190 |
| Net Income (Loss) ($M) | ($28.1) | ($39.3) | ($8.6) | $2.9 |
| Revenue Less Ancillary Services ($M) | $181.1 | $257.1 | $377.1 | $474.2 |
2024 Incentive Outcomes:
- Corporate metrics and payout determinations for cash incentives are shown above; CEO payout equaled 53.7% of target based on 0% revenue component and 107.5% EBITDA component .
Board Governance
- Board seat: Director since 2013; CEO and Director (not Chairman). The Board Chair is Phillip Riese; non-employee director compensation applies to independent directors; CEO receives no additional director compensation .
- Independence: All directors other than Mr. Massaro are independent per Nasdaq rules; independent directors hold executive sessions without Massaro or management present .
- Committees: People & Compensation Committee members are Diane Offereins (Chair), Matthew Harris, and Gretchen Howard; all are independent; committee oversees CEO pay, equity plans, clawback policy, and ownership guidelines .
- Classified board structure with three-year staggered terms, which can delay or prevent rapid changes in control or management .
Compensation Governance & Peer Group
- Compensation philosophy: pay-for-performance, majority equity; target total compensation positioned around 50th–75th percentile; no tax gross-ups; clawback policy administered by the People & Compensation Committee .
- 2024 compensation peer group: Asana, AvidXchange, EngageSmart (taken private Jan 2024), EVERTEC, JFrog, Lightspeed Commerce, nCino, Nuvei, PagerDuty, Payoneer Global, Phreesia, Remitly Global, Repay Holdings .
Related Policies and Risk Indicators
- Trading restrictions: No hedging or short sales; pledging allowed only with compliance clearance; Rule 10b5-1 plans permitted .
- No defined benefit pension or nonqualified deferred compensation plans .
- Equity grant policy: Grants not timed to MNPI; options exercise price must be ≥ FMV at grant; authority with People & Compensation Committee .
- Ownership guidelines: CEO 5x salary; executives and directors were compliant at year-end 2024 .
Investment Implications
- Alignment: Heavy equity mix with multi-year RSU vesting (25% one-year cliff, then quarterly over three years) supports retention and ties realized pay to stock performance; CEO met 5x ownership guideline, improving alignment with shareholders .
- Selling pressure: 2024 realized value on vesting ($4.36M) and option exercises ($2.09M) suggests ongoing liquidity events; RSU schedules create predictable vesting supply; hedging prohibited, but pledging allowed with clearance—monitor Form 4 activity and any pledges for incremental selling pressure risk .
- Incentive design: Annual bonus linked to Revenue Less Ancillary Services and Adjusted EBITDA provides balanced growth/profitability focus; 2024 missed revenue threshold but exceeded EBITDA target, yielding 53.7% payout—consistent pay-for-performance calibration .
- Change-in-control: Double-trigger acceleration with significant RSU value ($11.95M within CoC window) plus 1.5x cash multiple could influence negotiation stance in strategic scenarios—material economics to the CEO .
- Governance: CEO/Director dual role is mitigated by independent Chair, independent committees, and executive sessions; classified board and robust committee oversight reduce immediate governance concerns, but staggered terms can entrench leadership .