Senior Specialist, Benefits

Responsibilities

• Lead end-to-end benefits administration for the UK and Ireland, including enrollments, payroll integrations, and compliance.
• Manage external vendors and benefits providers, including contract negotiation and invoice oversight.
• Drive strategic planning by researching market trends and using data to benchmark and improve benefits offerings.
• Own the full lifecycle of benefits renewals and the implementation of new programs.
• Act as the subject matter expert for employee inquiries, troubleshooting system errors and resolving complex escalations.
• Collaborate cross-functionally with Payroll, People Onboarding, Finance, and Procurement teams.

Requirements

• Extensive experience in end-to-end benefits program management and strategy, specifically within the UK.
• Deep understanding of health, welfare, and retirement benefits administration.
• Proven track record in vendor management and overseeing complex benefits systems.
• Strong analytical skills with experience using data to drive strategic improvements.
• Advanced proficiency in Microsoft Excel, including PivotTables and VLOOKUPs.
• Experience using Workday or similar benefits platforms for reporting and plan updates.
• Excellent communication and presentation skills with the ability to explain complex information clearly.
• Ability to work autonomously and thrive in a fast-paced, high-growth environment.

Preferred Qualifications

• Experience working within a high-growth technology or FinTech company.

About the Company

Checkout.com is a leading global payments platform that enables businesses to deliver effortless digital experiences at scale. We power transactions for some of the world's most ambitious brands, including eBay, Spotify, and Uber. With 20 offices across six continents, we are shaping the future of fintech through innovation, diversity, and high-performance teams.