Senior Specialist, Benefits (MENA & APAC)

About Checkout.com

Checkout.com is a global fintech leader powering over 10 billion transactions each year for more than a billion shoppers worldwide. We enable seamless digital payments for prominent companies such as eBay, Spotify, Klarna, Uber, and Sony. With 20 offices spread across six continents and headquartered in London, we are rapidly shaping the future of financial technology.

Role Overview

We are seeking a self-driven Benefits Expert to lead the design, execution, and enhancement of our employee benefits programs primarily across the APAC and MENA regions. This role involves collaborating with leadership, onboarding teams, employees, and external vendors to provide competitive and comprehensive benefits while ensuring smooth delivery and compliance.

Key Responsibilities

• Manage daily operations of regional benefits programs including enrollments, payroll coordination, compliance adherence, and resolving employee queries with a customer-service focus.
• Act as the primary liaison for external benefits vendors: negotiate contracts with procurement, oversee invoicing, and maintain benefits platforms like AON efficiently.
• Conduct strategic analysis of beneficial offerings using market research and utilization data to recommend program improvements enhancing competitiveness and employee value.
• Lead annual benefits renewals and launch new programs, including employee surveys, communication plans, and presentations to improve awareness and engagement.
• Troubleshoot and resolve system issues and complex escalations to deliver a smooth benefits experience.
• Collaborate cross-functionally with Payroll, Onboarding, Finance, Accounting, and Procurement teams to ensure compliant and flawless benefits execution.
• Operate autonomously to maintain operational excellence and develop strategic benefits initiatives aligned with company growth.

Required Qualifications

• Proven experience managing complete benefits programs in MENA and APAC, including health, welfare, and retirement plans administration.
• Expertise in vendor management, contract negotiation, and benefits technology platforms.
• Strong analytical and strategic skills to evaluate data and market trends for benefits optimization.
• Track record of leading projects independently from planning to implementation with excellent problem-solving skills.
• Exceptional communication and presentation skills, conveying complex benefits information empathetically to diverse audiences.
• Strong interpersonal abilities to connect effectively with employees and management.
• Advanced proficiency in Google Sheets and Excel, with capability to automate and streamline workflows.
• Experience with Workday or similar benefits platforms, including managing open enrollment and reporting.
• Ability to thrive in a fast-paced, dynamic environment.

Additional Information

Checkout.com promotes an inclusive and supportive workplace enabling high performance and meaningful impact from day one. We encourage open communication to ensure accessibility and accommodation needs are met throughout the recruitment and employment experience. Our hybrid working model includes three days per week onsite to foster collaboration and connection.

Work Location

This position is based in Dubai, UAE, requiring presence onsite.