Benefits Lead

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.

• Lead Benefits Administration:
  Own and execute the day-to-day operations of our regional benefits programs across the Americas, including 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, negotiate contracts with our procurement team, oversee invoices, and manage our benefits systems, including AON and other platforms, to ensure they are efficient and accurate.
• Drive Strategic Planning and Benchmarking:
  Shape our benefits strategy beyond day-to-day tasks by researching market trends, using data to analyze plan utilization, recommending improvements to keep our offerings competitive and employee‑centric, and 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, surveying employees, creating and delivering engaging communications and presentations to 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, 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 such as Payroll, People Onboarding, Finance, and Procurement to ensure the smooth and compliant execution of all benefits programs, serving as the subject matter expert and key advisor to colleagues.
• Take Full Ownership:
  Work independently with a high degree of autonomy, managing the full scope of benefits for the Americas while ensuring operational excellence and long‑term strategic enhancements.

• 5+ years of Benefits Expertise: extensive experience managing end‑to‑end benefits programs, deep understanding of benefits strategy, design, and administration for the US and Canada; experience in Brazil and Mexico is a plus.
• 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.
• Strong understanding of benefits compliance and regulations, including US federal and state laws, US FMLA and leave administration in a multi‑state environment, and Workers’ Compensation, IRS, and ERISA regulations.
• Vendor and Systems Management: proven ability to manage vendors, negotiate contracts, and oversee benefits systems and platforms.
• 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, leading benefit renewals and new implementations from start to finish with minimal guidance.
• Excellent communication, written and verbal, and presentation skills with the ability to clearly articulate complex benefits information to employees and leadership, consistently demonstrating empathy, patience, and compassion.
• Excellent interpersonal skills, ability to connect with employees and management.
• Advanced Microsoft Excel skills, including proficiency with Pivot Tables and VLOOKUP functions.
• Experience using Workday, launching Open Enrollment, updating benefit plans, and running reports.

• Experience in a fast‑paced, high‑growth technology or Fin Tech environment.
• Professional certifications such as CEBS, PHR/SPHR.
• Fluency in Spanish.
• Fluency in Portuguese.

We believe in equal opportunities. We work as one team. Wherever you come from. However you identify.