Senior Benefits Specialist

About the role

Checkout.com is expanding rapidly and seeks a proactive Benefits SME to own the design, implementation and enhancement of its benefits programs across Europe and Mauritius. You will drive end‑to‑end benefits strategy and operations while collaborating with leadership, People Onboarding and external vendors.

Key responsibilities

• Own and execute day‑to‑day operations of regional benefits programs, handling enrollments, payroll integration, compliance and employee inquiries.
• Serve as primary contact for external benefits providers, negotiate contracts, oversee invoices and manage benefits systems such as AON.
• Research market trends, analyse utilisation data and recommend improvements to keep offerings competitive and employee‑centric.
• Lead benefits renewals and new program implementations, from employee surveys to communications and presentations.
• Troubleshoot system errors, resolve complex escalations and streamline processes for a seamless benefits experience.
• Partner with Payroll, People Onboarding, Finance, Accounting and Procurement as the subject‑matter expert.

Required profile

• Extensive experience managing end‑to‑end benefits programs in Europe and Mauritius, with deep knowledge of health, welfare and retirement plans.
• Proven ability to manage vendors, negotiate contracts and oversee benefits platforms, ensuring accurate administration and compliance.
• Strong analytical skills to use data for trend analysis, benchmarking and strategic recommendations.
• Demonstrated project leadership delivering benefit renewals and new implementations autonomously.
• Excellent communication and presentation skills, with empathy and patience when explaining complex benefits information.

Required skills

• Advanced Google Sheets and Excel proficiency, including automation and process optimisation.
• Experience with Workday or comparable benefits platforms for open enrollment, plan updates and reporting.
• Familiarity with benefits administration systems such as AON.