Global Benefits Manager

Flywire • Chicago, IL

77d • $115,000 - $140,000

About The Position

Flywire is seeking a Global Benefits Manager to lead the delivery and evolution of our global benefits and wellbeing programs. In this high-impact role, you’ll own our health, retirement, leave, and wellness offerings, ensuring programs are employee-centric, compliant, and scalable. A key initial focus will be on transitioning benefits administration to our Global People Service Center (GPSC) team, including workflow setup, process documentation, and coaching GPSC team to confidently handle employee-facing inquiries. Your ability to enable others while remaining hands-on will be key to building scalable operations and establishing yourself as the go-to expert for more complex issues. You will lead benefits planning, design and execution, manage vendor relationships, oversee compliance deliverables, and elevate the employee experience. You’ll also partner closely with Total Rewards leadership to shape future strategy. This is an ideal role for someone with a growth mindset who brings operational excellence and proactive, cross-functional partnership.

Requirements

• 5–8 years of experience in Global Benefits or Total Rewards, with demonstrated ownership of benefits program delivery in multinational environments
• Advanced knowledge of benefits plan design and administration, with a proactive mindset toward market trends and evolving best practices
• Strong understanding of the U.S. regulatory environment (e.g., ERISA, ACA, COBRA), with exposure to international benefits preferred
• Proven experience managing multiple vendors, including renewals, service-level oversight, and performance optimization
• Experience working with shared services or centralized operations teams (e.g., GPSC) to scale delivery and manage escalations
• Known for strong execution, problem-solving, and follow-through, with the ability to independently deliver across cross-functional stakeholders
• Strong analytical skills with working knowledge of Excel (e.g. formulas, pivot tables) to support data-driven decision making and reporting
• Excellent communicator, capable of translating complex benefit topics into clear, actionable messages for employees and internal partners

Nice To Haves

• Experience with Workday HRIS
• Exposure to international benefits

Responsibilities

• Serve as global lead for benefits program planning, design and delivery, across health, retirement, wellbeing, and leave programs
• Partner with GPSC to implement and refine workflows, document processes, and ensure operational consistency across regions
• Act as the primary escalation point for complex or sensitive benefits inquiries and issues
• Partner with Finance to track benefits spend, support budget forecasting, and analyze cost impacts of plan changes or growth
• Own vendor relationships, including renewals, service escalations, vendor performance reviews, and cost management
• Oversee compliance and regulatory deliverables (e.g. 5500 fillings, ACA reporting, eligibility and accuracy audits)
• Experience leading benefits-related design and configuration work during HRIS implementations; Workday experience strongly preferred
• Support ongoing benefits communications, education campaigns, and employee facing materials
• Contribute to benefits analytics and reporting, plan benchmarking, design analysis, and program enhancement in partnership with vendors / brokers
• Partner with Total Rewards leadership on long-term benefits strategy and continuous improvement initiatives

Benefits

• Competitive compensation, including Restricted Stock Units
• Employee Stock Purchase Plan (ESPP)
• Flying Start - Our immersive Global Induction Program
• Dynamic & Global Team
• Wellbeing Programs (Mental Health, Wellness)
• Competitive time off including FlyBetter Days to volunteer in a cause you believe in and Digital Disconnect Days
• Great Talent & Development Programs

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 1,001-5,000 employees