🧾 What This Document Is

This is Flywire's definitive proxy statement (DEF 14A) for its 2026 Annual Meeting of Stockholders.
👉 In simple terms: It’s the "voter guide" for shareholders, explaining what they’ll vote on, who’s running the company, and how executives are paid.
The meeting is virtual on June 2, 2026, at 9:30 a.m. EDT. Shareholders as of April 8, 2026, can vote.

🏢 What The Company Does

Flywire is a global payments platform that specializes in complex, high-value transactions for industries like education, healthcare, and travel.
👉 Think of them as a digital payments bridge connecting institutions (like universities or hospitals) with payers (like international students or patients) across borders.
They handle currency conversion, payment plans, and compliance.

📋 Key Proposals for Shareholders

Shareholders will vote on three main items:

ELECT DIRECTORS
- Nominees: Alex Finkelstein (Spark Capital), Matthew Harris (Bain Capital Ventures), Gretchen Howard (ex-Robinson Hood COO).
- Why it matters: The board oversees the company’s direction. These nominees bring venture capital, payments, and operational expertise.
RATIFY AUDITORS
- Firm: PricewaterhouseCoopers LLP (PwC).
- Why it matters: Shareholders approve the independent auditor. PwC has been Flywire’s auditor since 2012.
APPROVE EXECUTIVE COMPENSATION (ADVISORY VOTE)
- A non-binding vote on how top executives are paid.
- Why it matters: It signals shareholder sentiment on pay practices, even if not legally binding.

👉 The board recommends "FOR" on all three proposals.

💰 Executive Compensation Insights

Flywire’s philosophy: Pay-for-performance with heavy equity weighting.
Key practices:
✅ Majority of compensation in stock awards (aligned with long-term value).
✅ One-year post-vesting holding requirement for executive equity (new in 2026).
✅ Clawback policy to recover wrongly awarded bonuses.
❌ No tax gross-ups, hedging, or guaranteed bonuses.

👉 2025 Highlights:

CEO Michael Massaro’s total compensation: $10.8 million (mostly equity).
Other NEOs: Total comp ranged from $4.2M to $6.1M.
Peer group: Compared to tech/payments companies like PayPal, Block, and StoneCo.

👥 Board & Governance

Board Structure: 9 members, divided into 3 classes with staggered terms.
Independence: 8 of 9 directors are independent (excluding CEO).
Committees:

Audit Committee (oversees financial reporting, risk).
People & Compensation Committee (sets executive pay).
Nominating & Corporate Governance Committee (director nominations, governance).

👉 New director in 2026: Christine Katziff (ex-Bank of America Audit Chief).
Meetings in 2025: Board met 6 times; all directors attended >75% of meetings.

⚖️ Big Picture: Strengths & Risks

👍 Strengths:

Strong alignment of pay with performance (equity-heavy).
Diverse board with payments, tech, and finance expertise.
Transparent governance and shareholder engagement (e.g., 2025 outreach on pay).

⚠️ Risks:

Staggered board could delay change-of-control.
Heavy reliance on equity compensation may dilute shares over time.
Global operations expose to regulatory and currency risks.

🌍 Industry Context

Flywire operates in cross-border payments, a competitive sector facing:

Pressure from fintech disruptors (e.g., Wise, Stripe).
Regulatory scrutiny on compliance and fees.
Demand for faster, cheaper international transactions.

👉 Their niche: Vertical-specific software (education, healthcare) bundled with payments, creating stickier client relationships.

🔮 What’s Next

Annual Meeting: June 2, 2026 – shareholders will vote on proposals.
2026 Priorities: Expand in healthcare and travel verticals, enhance payment solutions.
Compensation Changes: New one-year holding period for executive equity starting 2026.

🧠 The Analogy

Imagine Flywire as a global airport for money.

The annual meeting is like the airport’s annual safety review – shareholders check the "flight crew" (board) and "maintenance plans" (auditors).
Executive pay is the crew’s incentive program – tied to on-time flights (performance) and passenger satisfaction (shareholder returns).
The new holding rule ensures pilots keep skin in the game long after landing.

🧩 Final Takeaway

Flywire’s proxy highlights a stable board, shareholder-aligned pay, and a focus on long-term growth in competitive cross-border payments. The key votes are about electing experienced directors, ratifying trusted auditors, and endorsing an executive pay structure that emphasizes equity and accountability.

Flywire Shareholders Vote on Board, Auditors, and Pay