Senior Specialist, Benefits

Company Description We’re Checkout.com – you might not know our name, but companies like eBay, ASOS, Klarna, Uber Eats, and Sony do. That moment when you check out online? We make it happen. Checkout.com is where the world checks out. Our global network powers billions of transactions every year, making money move without making a fuss. We spent years perfecting a service most people will never notice. Because when digital payments just work, businesses grow, customers stay, and no one stops to think about why. With 19 offices spanning six continents, we feel at home everywhere – but London is our HQ. Wherever our people work their magic, they’re fast-moving, performance-obsessed, and driven by being better every day. Ideal. Because a role here isn’t just another job; it’s a career-defining opportunity to build the future of fintech. Job Description As we continue our rapid growth, we're seeking a proactive Benefits SME to take ownership of designing, implementing, and enhancing our benefits programs across the Americas Region (strong focus in the US, Canada and Brazil but may expand over time). You'll drive the end-to-end benefits strategy and operations, collaborating closely with Checkout leadership, People Onboarding, and external vendors, as well as employees, to build best-in-class benefits offerings while ensuring seamless delivery. If you excel at balancing strategic thinking with hands-on execution, leveraging data-driven insights, and tackling challenges in a dynamic environment, we'd love to discuss how you can contribute to our journey! What You’ll Be Doing Lead Benefits Administration: You'll own and execute the day-to-day operations of our regional benefits programs across the Americas. This includes managing enrollments, ensuring seamless payroll integrations, handling compliance, and resolving employee inquiries with a strong focus on exceptional service. Manage Vendors and Systems: Serve as the primary point of contact for external benefits providers and partners. You'll negotiate contracts with our procurement team, oversee invoices, and manage our benefits systems, including AON and other platforms, to ensure they're efficient and accurate. Drive Strategic Planning and Benchmarking: Go beyond day-to-day tasks by actively shaping our benefits stirategy. You'll research market trends, use data to analyze plan utilization, and recommend improvements to ensure our offerings are competitive and employee-centric. You'll also be responsible for developing and presenting a long-term benefits roadmap to leadership. Manage Renewals and Implementations: Take full ownership of benefits renewals and new program implementations throughout the year. This involves everything from surveying employees to creating and delivering engaging communications and presentations that help our people understand the full value of their benefits. Solve Problems and Handle Escalations: Act as the go-to expert for all benefits-related issues. You'll troubleshoot system errors, resolve complex employee escalations, and streamline processes to ensure a seamless benefits experience for everyone. Collaborate Cross-Functionally: Partner closely with internal teams like Payroll, People Onboarding, Finance, and Procurement to ensure the smooth and compliant execution of all benefits programs. You'll serve as the subject matter expert and a key advisor to your colleagues. Take Full Ownership: This is a role for a true self-starter. You'll be expected to work with a high degree of autonomy, independently managing the full scope of benefits for the Americas while ensuring both operational excellence and long-term strategic enhancements. Required Qualifications 5 years of Benefits Expertise: Extensive experience managing end-to-end benefits programs, with a deep understanding of benefits strategy, design, and administration for the US and Canada. Experience with benefits in Brazil and Mexico is a plus. In-depth understanding of key he ... (truncated, view full listing at source)