checkout.com - Senior Specialist, Benefits
Requirements
• 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 demonstrating empathy, patience, and compassion. • Excellent interpersonal skills, with the ability to connect with employees and management. • Advanced Microsoft Excel skills, including proficiency with PivotTables, VLOOKUP functions. • Ability to thrive in a fast-paced work environment. • Experience using Workday and/or an alternative benefits platform, including launching Open Enrollment, updating benefit plans, and running reports. • Experience in a fast-paced, high-growth technology or FinTech environment. • It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable. • Life at Checkout.com http://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 https://www.checkout.com/careers to learn more about our culture, open roles, and what drives us. • For a closer look at daily life at Checkout.com http://Checkout.com, follow us on LinkedIn https://www.linkedin.com/company/checkout/life/ and Instagram https://www.instagram.com/checkout_com/
Responsibilities
• 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.
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