Senior Specialist, Benefits

Overview Company Description 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 are 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, external vendors, and 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 DoingLead Benefits Administration: Own and execute the day-to-day operations of regional benefits programs across the Americas, including enrollments, payroll integrations, compliance, and resolving employee inquiries with exceptional service.Manage Vendors and Systems: Serve as the primary point of contact for external benefits providers and partners. Negotiate contracts with our procurement team, oversee invoices, and manage benefits systems (including AON and other platforms) for efficiency and accuracy.Drive Strategic Planning and Benchmarking: Shape our benefits strategy, research market trends, analyze plan utilization, and recommend improvements to ensure offerings are competitive and employee-centric. Develop and present a long-term benefits roadmap to leadership.Manage Renewals and Implementations: Own renewals and new program implementations, including surveying employees and delivering engaging communications and presentations to help employees understand their benefits’ full value.Solve Problems and Handle Escalations: Act as the go-to expert for all benefits-related issues, troubleshoot system errors, resolve escalations, and streamline processes for a seamless benefits experience.Collaborate Cross-Functionally: Partner with Payroll, People Onboarding, Finance, and Procurement to ensure smooth and compliant execution of all benefits programs. Serve as a subject matter expert and advisor to colleagues.Take Full Ownership: Work with autonomy to manage the full scope of benefits for the Americas while ensuring operational excellence and long-term strategic enhancements.Required Qualifications5+ years of Benefits Expertise: End-to-end benefits program management, with deep experience in the US and Canada; experience with Brazil and Mexico is a plus.In-depth understanding of health, welfare, and retirement benefits administration functions, including vendor coordination, changes, life events, appeals, and annual enrollment.Strong understanding of benefits compliance and regulations, including US federal and state laws, FMLA and leave administration in a multi-state environment, Workers’ Compensation, IRS, and ERISA.Vendor and Systems Management: Experience managing vendors, negotiating contracts, and overseeing benefits systems and platforms. Comfortable with complex administrative processes.Strategic & Analytical Skills: Data-driven analysis of trends, benchmarking, and recommendations for strategic improvements to benefits offerings.Project Leadership: Proactive project management, including renewals and new implementations, with minimal guidance.Excellent communication and presentation skills; ability to explain complex benefits clearly with empathy and professionalism.Interpersonal skills to connect with employees and management.Advanced Microsoft Excel skills (PivotTables, VLOOKUP).Ability to thrive in a fast-paced environment.Experience using Workday (Open Enrollment, updating plans, running reports).Preferred QualificationsExperience in a fast-paced, high-growth technology or FinTech environment.Professional certifications (e.g., CEBS, PHR/SPHR).Fluency in Spanish.Fluency in Portuguese.Additional InformationApply without meeting all requirements stated.If you don’t meet all the requirements but think you might still be right for the role, please apply anyway. We’re always keen to speak to people who connect with our mission and values.We believe in equal opportunities.We work as one team. Wherever you come from. However you identify. And whichever payment method you use.Our clients come from all over the world — and so do we. Hiring hard-working people and giving them a community to thrive in is critical to our success.When you join our team, we’ll empower you to unlock your potential so you can do your best work.We’d love to hear how you think you could make a difference here with us.We want to set you up for success and make our process as accessible as possible. Let us know in your application or tell your recruiter if you need anything to make your experience or working environment more comfortable.Take a Peek Inside Life At Checkout.comOur Culture video https://youtu.be/BEwnpHuadSwOur careers page https://www.checkout.com/careersOur LinkedIn Life pages bit.ly/3OaoN1ULife at Checkout.com We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection. Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us. For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram.#J-18808-Ljbffr