Global Benefits Manager, Flywire
$115-140k
+ RSUs
Global payments processing
Be an early applicant
Global payments processing
1001+ employees
Be an early applicant
$115-140k
+ RSUs
1001+ employees
Company mission
To save international students and their families money that would otherwise be lost on bank fees and unfavorable foreign exchange rates.
Role
Who you are
- 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
What the job involves
- 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
Our take
Flywire is a digital platform that simplifies the paying experience for international transactions. Flywire leverages its vertical-specific software and payments technology to deeply embed within client's existing accounts-receivable workflows.
Flywire was first set up to help international students pay their tuition for American colleges, but has since grown into a global payments enablement and software company. It has processed billions of dollars in payments for clients across the world and recently secured approval for its major payment institution license, enabling it to operate domestic money transfer and cross-border money transfer services.
Flywire serves clients across education, healthcare, travel, and B2B, including several Ivy League schools, and top US hospital systems. The company appears to be focussed on growth, including by strategic acquisitions and entry into new markets, recently in the Asia Pacific and Australia, as well as further developing its channel partners ecosystem.
Steph
Company Specialist at Welcome to the Jungle
Insights
12% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Mar 2021
$60m
SERIES F
Feb 2020
$120m
SERIES E
Total funding: $323.2m
Company benefits
- Competitive compensation, including Restricted Stock Units
- Employee Stock Purchase Plan (ESPP)
- Flying Start - Our immersive Global Induction Program (Meet our Execs & Global Teams)
- 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, Yoga/Pilates/HIIT Classes) 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!
- Work From Home Stipend
- Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers!)
Company HQ
Boston, MA
Leadership
Mike Massaro
(CEO, not founder)Consultant at PwC. VP Strategic Accounts at Carrier IQ, before joining Flywire as VP Business Development in 2013. Became CEO upon departure of founder Iker Marcaide in 2013.
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