Manager/Sr Manager, Global Benefits at Flywire

Boston, Massachusetts, United States -

Full Time

Start Date

Immediate

Expiry Date

18 Feb, 26

Salary

170000.0

Posted On

20 Nov, 25

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Global Benefits Expertise, Benefits Strategy, Vendor Management, Data Analysis, Financial Modeling, Compliance Oversight, Benefits Communication, Operational Excellence, Process Improvement, Employee Experience

Industry

Software Development

Description

Company Description Are you ready to trade your job for a journey? Become a FlyMate! Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world. What more do we need to truly be unstoppable? Perhaps, that is you! Who we are: Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world. Today we support more than 4,800 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies. With over 1,200 global FlyMates, representing more than 40 nationalities, and in 12 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow. Job Description The Opportunity: Flywire is seeking a Global Benefits Manager to lead the strategy, delivery, and evolution of our global benefits and wellbeing programs. You will own our health, retirement, leave, and wellness offerings while ensuring they remain competitive, compliant, and aligned to a consistent global philosophy. A central responsibility will be full ownership of the annual global benefits strategy cycle including planning, design, renewal, forecasting, and multi year roadmap creation. You will also define and maintain a clear benefits philosophy that balances cost, competitiveness, value, and employee experience. This includes directing brokers with confidence, shaping strategy independently, and using vendor data, performance trends, and market benchmarks to guide decision making. An early focus will include transitioning benefits administration into our Global People Service Center (GPSC) by building workflows, documenting processes, and strengthening operational consistency. You will serve as the primary escalation point for complex issues and partner closely with Total Rewards leadership, Finance, GPSC, and external vendors to ensure seamless delivery. What You Will Do 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. Qualifications Here’s What We’re Looking For: 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. Additional Information What We Offer: Competitive compensation, including Restricted Stock Units Employee Stock Purchase Plan (ESPP) Flying Start - Our immersive Global Induction Program Work with brilliant people that will keep you on your toes, learn more about their journeys by checking out #InsideFlywire on social media Dynamic & Global Team (we have been collaborating virtually for years!) Wellbeing Programs (Mental Health, Wellness) with Global FlyMates Be a meaningful part in our success - every FlyMate makes an impact Competitive time off including FlyBetter Days to volunteer in a cause you believe in and Digital Disconnect Days! Great Talent & Development Programs Submit today and get started! We are excited to get to know you! Throughout our process you can expect to meet with different FlyMates including the Hiring Manager, Peers on the team, the VP of the department, and a skills assessment. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for any questions. The US base salary range for this full-time position is $115,000 - $170,000 plus restricted stock units and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training. Your Talent Acquisition Partner can share more about the specific salary range for your preferred location during the hiring process. Flywire is an equal opportunity employer. With over 30 nationalities across 12 different offices, and diversity and inclusion at the core of our people agenda, we believe our FlyMates are our greatest asset, and we’re excited to watch our unique culture evolve with each new hire. Flywire is an equal opportunity employer. #LI-Hybrid

Responsibilities

Lead the strategy, delivery, and evolution of global benefits and wellbeing programs. Oversee the annual global benefits strategy cycle, ensuring offerings remain competitive and compliant.