Senior Specialist, Regional People Partnering

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!

• 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.

• 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.
• Proven ability to manage vendors, negotiate contracts, and oversee benefits systems and platforms. Comfortable navigating complex administrative processes.
• Experience using data to analyze trends, benchmark against the market, and recommend strategic improvements to benefits offerings.
• Hands‑on, proactive project leadership, capable of managing projects and solving problems autonomously, including benefit renewals and new implementations with minimal guidance.
• Excellent communication, written, 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 Pivot Tables and 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 Fin Tech environment.