Senior Specialist, Benefits

Company Description We’re http://checkout.comCheckout.com http://Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day. We are where the world checks out, enabling over 10 billion transactions daily for more than one billion global shoppers. Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale. If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact. With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started. Company Description Checkout.com http://Checkout.com is one of the most exciting fintechs in the world. Our mission is to enable businesses and their communities to thrive in the digital economy. We’re the strategic payments partner for some of the best known fast-moving brands globally such as Wise, Hut Group, Sony Electronics, Homebase, Henkel, Klarna and many others. Purpose-built with performance and scalability in mind, our flexible cloud-based payments platform helps global enterprises launch new products and create experiences customers love. And it's not just what we build that makes us different. It's how. We empower passionate problem-solvers to collaborate, innovate and do their best work. That’s why we’re on the Forbes Cloud 100 list and a Great Place to Work accredited company. And we’re just getting started. We’re building diverse and inclusive teams around the world — because that’s how we create even better experiences for our merchants and our partners. And we need your help. Join us to build the digital economy of tomorrow. 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 alongside the Global Benefits Manager, with a focus on the UK and Ireland, however this may expand over time. You'll drive the end-to-end benefits strategy and operations, collaborating closely with Checkout Regional People leaders, 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 in the UK and Ireland. 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 strategy. You'll research market trends, use data to analyze plan utilization, and recommend improvements to ensure our offerings are competitive and employee-centric. - 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 ensuring both operational excellence and long-term strategic enhancements. Qualifications Required Qualifications - Extensive experience managing end-to-end benefits programs, with a deep understanding of benefits strategy, design, and administration in the UK (and Ireland preferred but non-essential) - In-depth understanding of key health, welfare, and retirement benefits administration functions, including vendor coordination, handling employee changes, processing qualifying life events and appeals, and managing annual enrollment. - Vendor and Systems Management: Proven ability to manage vendors, negotiate contracts, and oversee benefits systems and platforms. You should be comfortable navigating complex administrative processes. - Strategic & Analytical Skills: Experience using data to analyze trends, benchmark against the market, and recommend strategic improvements to benefits offerings. - Project Leadership: A hands-on, proactive approach to managing projects and solving problems autonomously. You should be comfortable leading benefit renewals and new implementations from start to finish with minimal guidance. - Excellent communication, both written and verbal, and presentation skills, with the ability to clearly articulate complex benefits information to employees and leadership while consistently demonstrat