Benefits Lead

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 will 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.

What You'll Be Doing

• Lead Benefits Administration: Own and execute day‑to‑day operations of our regional benefits programs across the Americas. Manage enrollments, ensure seamless payroll integrations, handle compliance, and resolve 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 procurement, oversee invoices, and manage benefits systems (e.g., AON and other platforms) to ensure they are efficient and accurate.
• Drive Strategic Planning and Benchmarking: Shape our benefits strategy by researching market trends, analyzing plan utilization data, and recommending improvements. Develop and present a long‑term benefits roadmap to leadership.
• Manage Renewals and Implementations: Take full ownership of benefits renewals and new program implementations throughout the year, including employee surveys and compelling communications that help 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 all.
• Collaborate Cross‑functionally: Partner closely with teams such as Payroll, People Onboarding, Finance, and Procurement to ensure smooth, compliant execution of all benefits programs. Serve as the subject‑matter expert and advisor to colleagues.
• Take Full Ownership: Work as a self‑starter with a high degree of autonomy, independently managing the full scope of benefits for the Americas while ensuring operational excellence and long‑term strategic enhancements.

Required Qualifications

• 5+ years of Benefits Expertise: Extensive experience managing end‑to‑end benefits programs, with deep knowledge 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 knowledge of benefits compliance and regulations, including US federal and state laws, US FMLA and leave administration in a multi‑state environment, 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: Hands‑on, proactive approach to managing projects and solving problems autonomously. Comfortable 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 while 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 and VLOOKUP functions.
• Ability to thrive in a fast‑paced work environment.
• Experience using Workday, including launching Open Enrollment, updating benefit plans, and running reports.

Preferred Qualifications

• Experience in a fast‑paced, high‑growth technology or FinTech environment.
• Professional certifications (e.g., CEBS, PHR/SPHR).
• Fluency in Spanish.
• Fluency in Portuguese.

Equal Opportunity Statement

We believe in equal opportunities. We work as one team, no matter how you identify. We welcome applicants from all backgrounds and settings.