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Flywire

Global payments platform for education, healthcare

Vice President, Product Payments Experience & Customer Loyalty

Full-TimeUpdated on 10/14/2026
No salary listed
Expert
Singapore
Hybrid
ProductProduct Management

About the job

Requirements
  • 15+ years of Product Management experience, including at least 5 years leading organizations at the Vice President level or equivalent.
  • Extensive experience owning global consumer payment products or fintech platforms serving millions of users.
  • Proven success improving payment conversion, customer engagement, and user experience across complex international payment ecosystems.
  • Demonstrated experience building customer loyalty, retention, or recurring engagement programs within payments or financial technology.
  • Strong product strategy background and experience modernizing large-scale platforms and consolidating legacy products.
  • Deep understanding of user experience, product design, localization, accessibility, and customer-centric product development.
  • Experience partnering with engineering organizations to deliver highly scalable payment platforms.
  • Knowledge of regulated payment markets including India, China, or similar international markets.
  • Ability to influence senior leadership, executive committees, and Board-level stakeholders.
  • Experience leveraging experimentation, product analytics, customer insights, and artificial-intelligence-enabled product development.
  • Experience with artificial-intelligence-powered product development and personalization; product analytics tools such as Amplitude, Mixpanel, Looker, or Tableau; experimentation and A/B testing platforms; Figma; Jira; Confluence; global payments platforms; payment APIs; cloud-native software-as-a-service platforms; and data and customer insights platforms.
Responsibilities
  • Define the vision and strategy for every payer-facing payment experience across the global payments platform.
  • Own Hosted Payment Pages, Checkout, payment flows, translations, notifications, email communications, and overall user experience.
  • Establish global quality standards and ensure consistent experiences across products and regions.
  • Improve payment completion, conversion, and customer satisfaction through continuous optimization.
  • Lead localization strategies across highly regulated global markets, including India, China, and other complex regions.
  • Build Flywire's first global payer loyalty strategy.
  • Increase repeat payment behavior through frictionless returning-payer experiences.
  • Develop loyalty metrics including repeat usage, retention, re-engagement, and lifetime value.
  • Partner with Payments Monetization to balance customer experience with sustainable business outcomes.
  • Evaluate loyalty initiatives, referrals, personalized experiences, and value-added payment services.
  • Lead consolidation of fragmented payer experiences into a unified global platform.
  • Define long-term experience architecture alongside Platform Engineering.
  • Prioritize modernization initiatives that improve scalability, maintainability, and user experience.
  • Simplify customer journeys while reducing operational complexity.
  • Serve as the executive advocate for the payer.
  • Translate customer feedback, behavioral insights, and market trends into product investments.
  • Partner with Payments Performance & Insights to identify friction and optimization opportunities.
  • Influence strategic decisions across Product, Platform Engineering, Network, Operations, and Commercial teams.
  • Lead and develop a global Product Management organization.
  • Foster a culture of experimentation, rapid learning, and data-driven decision-making.
  • Partner closely with Engineering, Design, Analytics, Payments Network, Operations, and Commercial leaders.
  • Drive AI-first product development practices using AI-assisted product discovery, personalization, and rapid iteration throughout the product lifecycle.
Desired Qualifications
  • Preferred experience with AI-powered product development and personalization; product analytics tools such as Amplitude, Mixpanel, Looker, or Tableau; experimentation and A/B testing platforms; Figma; Jira; Confluence; global payments platforms; payment APIs; cloud-native software-as-a-service platforms; and data and customer insights platforms.

About the company

Flywire provides global payments enablement and software for high-value cross-border payments across education, healthcare, travel, and B2B. It combines a payments platform, a global network, and vertical-specific software to manage invoicing, payment, and receivables, integrating with clients' ERP and A/R systems; it supports 140+ currencies across 240+ countries and local currency payments with installment options. It differentiates itself by vertical-focused software and end-to-end receivables workflow embedded in clients' systems rather than a generic processor. Its goal is to simplify and streamline complex, high-value payments for institutions and enterprises worldwide while expanding its geographic and industry reach.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

Boston, Massachusetts

Founded

2011

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Simplify's Take

What believers are saying

  • Q2 2026 revenue rose 27.2% to $167.7 million, with EBITDA margin 14.6%.
  • Davidson Hospitality expanded Flywire on Sept. 9, 2026, signaling repeatable travel expansion.
  • Trustly and AI automation cut support tickets 40%, improving unit economics and retention.

What critics are saying

  • Education still depends on visa policy; Flywire assumed a 30% decline in 2026.
  • Gross margin fell to 53.4% in Q2 2026, squeezing monetization from growth.
  • CEO and directors sold stock in September 2026 while execution relies on complex integrations.

What makes Flywire unique

  • Flywire’s Sept. 23, 2026 board pick, Sabrina Farmer, reinforces infrastructure-heavy payments scale.
  • Its Sertifi travel software plus payments stack keeps winning global hospitality workflows.
  • Flywire’s vertical focus spans education, healthcare, travel, and B2B, not commoditized checkout.

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Benefits

  • Health Insurance
  • 401(k) Retirement Plan
  • Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-3%

2 year growth

-1%
Yahoo Finance
Sep 23rd, 2026
Flywire expands hotel payment platform with Davidson after Q2 revenue jumps 27%

Flywire expanded its partnership with Davidson Hospitality Group on 9 September, rolling out its payment and e-signature platform across Davidson's full hotel portfolio. Properties using the tools saw signature turnaround times drop by roughly 75% and achieved savings on processing fees within months. The deal follows a strong second quarter in which Flywire's revenue rose 27.2% year over year to $167.7 million, and total payment volume jumped 38.2% to $8.2 billion. Adjusted EBITDA climbed 44.5% to $24 million, lifting the margin to 14.6%. The company raised its full-year revenue growth guidance by 300 basis points at the midpoint. However, gross margin slipped to 53.4% from 57% a year earlier. Flywire remains unprofitable on a GAAP basis, posting a net loss of $8.1 million in the quarter.

Yahoo Finance
Aug 13th, 2026
Flywire beats Q2 revenue estimates with $164M, guides Q3 above expectations at $231M

Flywire reported second quarter results that beat analyst expectations on revenue and adjusted EBITDA. The company posted revenue of $163.8 million, up 28.5% year-on-year and 4.5% above estimates. Adjusted EBITDA came in at $24.04 million, beating forecasts by 11.4%. CEO Michael Massaro attributed the performance to broad-based growth across education, travel, and B2B payments. The company's guidance for third quarter revenue of $231 million exceeded analyst estimates of $229.1 million. During the earnings call, analysts probed management on proposed US visa regulations, business mix at $1 billion revenue, cross-sell opportunities, margin dynamics between domestic and cross-border volumes, and AI implementation costs. Flywire said its guidance assumes a prudent 30% visa decline and noted that digital transformation investments are driving productivity gains.

Yahoo Finance
Aug 5th, 2026
Flywire beats Q2 expectations with 28% revenue growth to $164M, raises 2026 outlook

Flywire exceeded second-quarter expectations, with revenue less ancillary services rising 28% year-over-year to $164 million and adjusted EBITDA reaching $24 million. Transaction revenue increased 35% to $135.9 million, supported by 43% growth in transaction payment volume. Travel, hospitality, healthcare, and B2B payment-processing drove growth. The company raised its 2026 outlook to 21%–27% FX-neutral revenue growth and approximately 23% adjusted EBITDA margin at midpoint. Flywire projects more than $50 million in GAAP net income and 70%–75% free-cash-flow conversion. The company remains cautious about international education due to visa and regulatory pressures, but is diversifying geographically and expanding its Student Financial Services platform, hospitality business, and AI-driven automation initiatives.

Yahoo Finance
Aug 3rd, 2026
Flywire expects 22.8% revenue growth ahead of Q2 earnings report

Flywire will report Q2 earnings on Tuesday after market hours. The global payments company beat revenue expectations last quarter with $184 million, up 42.9% year-on-year. Analysts expect Q2 revenue to grow 22.8% year-on-year, down from the 27.7% increase in the same quarter last year. Analysts have largely reconfirmed their estimates over the past 30 days. Flywire has missed Wall Street's revenue estimates multiple times over the last two years. The finance and HR software segment has seen positive investor sentiment, with share prices up 2.7% on average over the last month. Flywire's shares are down 12.7% during the same period. The stock currently trades at $16.01, below the average analyst price target of $19.31.

Yahoo Finance
Jul 5th, 2026
Flywire reports 41% revenue growth as US-Iran ceasefire could boost travel payments

Flywire and Airbnb could benefit from a potential US-Iran ceasefire, which may boost consumer confidence, lower fuel costs, and restore flight routes. Flywire, a global payments enablement company, reported 41% year-over-year revenue growth in Q1 2026. Analysts project earnings growth of approximately 111% in the coming year. The company facilitates cross-border transactions across travel, education, healthcare, and commercial services. Airbnb's revenue rose 18% year-over-year to $2.7 billion. The company estimates the Middle East conflict weighed about 100 basis points on nights and seats. A post-ceasefire scenario could increase stability in the travel industry. Both companies stand to benefit from increased international travel, though the extent of benefits may vary across different global regions.