Flywire · 2 months ago
Manager/Sr Manager, Global Benefits
Boston, MA, USA
Full-time
Onsite
Senior Level
$115K/yr - $170K/yr
5+ years expFlywire is a global payments enablement and software company seeking a Global Benefits Manager to lead the strategy and delivery of their global benefits and wellbeing programs. The role involves overseeing health, retirement, leave, and wellness offerings, ensuring they are competitive and compliant while enhancing employee experience.
Financial ServicesFinTechPaymentsService IndustrySoftware
Responsibilities
Own the full global benefits strategy cycle, including annual planning, design, budgeting, renewal, and creation of a multi year benefits roadmap grounded in strong rationale and aligned to cost, competitiveness, value, and employee experience
Lead global benefits program delivery across health, retirement, wellbeing, and leave plans while directing brokers, optimizing vendor performance, managing renewals, and analyzing global cost levers to improve value and regional spend
Build scalable operations by partnering with the GPSC to create workflows, document processes, and transition administrative responsibilities while serving as the escalation point for complex or sensitive issues
Drive data informed strategy by analyzing vendor data, utilization trends, benchmarks, and plan performance to support financial modeling, forecasting, and strategic adjustments
Ensure global compliance and accuracy by overseeing regulatory deliverables, eligibility audits, accuracy reviews, and HRIS configuration, including Workday benefits design and updates
Elevate benefits communication and employee experience by designing clear and engaging materials, leading education campaigns, and partnering cross functionally to improve understanding and satisfaction across regions
Qualification
Required
Proven global benefits expertise, ideally five to eight years, with demonstrated ownership of strategy, delivery, and analysis across multinational environments
Experience building and executing multi year benefits roadmaps and defining a benefits philosophy that balances cost, competitiveness, employee experience, and long term value
Strong broker and vendor leadership, with the ability to set strategy, influence decisions, manage renewals, and use performance data and regional cost levers to optimize spend
Advanced analytical and financial skills, including comfort with Excel, data modeling, forecasting, plan performance evaluation, and benchmarking to guide improvements
Operational excellence in scaling benefits delivery, including partnering with shared services, managing escalations, improving processes, and supporting HRIS design and configuration
Exceptional communication and sound judgment, with the ability to translate complex benefit topics clearly, resolve issues quickly, and balance strategic priorities with hands on execution
Benefits
Competitive compensation, including Restricted Stock Units
Employee Stock Purchase Plan (ESPP)
Flying Start - Our immersive Global Induction Program
Dynamic & Global Team (we have been collaborating virtually for years!)
Wellbeing Programs (Mental Health, Wellness) with Global FlyMates
Competitive time off including FlyBetter Days to volunteer in a cause you believe in and Digital Disconnect Days!
Great Talent & Development Programs
Company
Flywire
Flywire is a payments enablement and software company that simplifies complex payments for its clients and their customers.
1001-5000 employees
Funding
Current Stage
Public CompanyTotal Funding
$583.3MKey Investors
Goldman SachsTemasek HoldingsBain Capital Ventures
2023-08-09Post Ipo Equity· $260.1M
2021-05-26IPO
2021-03-04Series F· $60M
Leadership Team
Mike Massaro
Chief Executive Officer
David King
Chief Technology Officer
Recent News
2026-01-05
2025-12-09
2025-12-04
Company data provided by crunchbase