Global Benefits Manager at Flywire

Chicago, Illinois, United States -

Full Time

Start Date

Immediate

Expiry Date

17 Jan, 26

Salary

140000.0

Posted On

19 Oct, 25

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Global Benefits, Total Rewards, Benefits Program Delivery, Vendor Management, Compliance, HRIS Implementations, Analytical Skills, Communication Skills, Problem-Solving, Operational Excellence, Cross-Functional Partnership, Budget Forecasting, Employee Experience, Process Documentation, Wellbeing Programs, Benefits Analytics

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 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. 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. Qualifications Here’s What We’re Looking For: 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 partner Open to Boston or Chicago 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 - $140,000 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-Remote

Responsibilities

Lead the delivery and evolution of global benefits and wellbeing programs, ensuring they are employee-centric and compliant. Manage vendor relationships, oversee compliance deliverables, and partner with Total Rewards leadership to shape future strategy.