Benefits Lead

0011 Checkout LLC; Atlanta (GA); On-site; USD 90,000 - 120,000; Full time

Job summary

0011 Checkout LLC is looking for a Benefits SME who will take ownership of designing and implementing benefits programs across the Americas, primarily focusing on the US, Canada, and Brazil. This role requires leading benefits administration, managing vendor relations, and driving strategic planning.

The ideal candidate should have over 5 years of benefits expertise, strong communication skills, and a solid understanding of compliance regulations. Proficiency in Excel and benefits management systems is crucial.

Qualifications

• 5+ years of extensive experience managing end-to-end benefits programs, particularly in the US and Canada.
• Strong understanding of benefits compliance and regulations, including US federal and state laws.
• Proficiency in using data to analyze trends and recommend strategic improvements.

Responsibilities

• Own and execute day-to-day operations of regional benefits programs.
• Serve as the primary point of contact for external benefits providers.
• Lead strategic planning and benchmarking efforts to enhance benefits offerings.

Skills

Benefits Management

Vendor Management

Regulatory Compliance

Strategic Planning

Project Leadership

Microsoft Excel

Communication Skills

Tools

Workday

Job description

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.

What You’ll Be Doing

• 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.

Required Qualifications

• 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 PivotTables and VLOOKUP functions.
• Experience using Workday, launching Open Enrollment, updating benefit plans, and running reports.

Preferred Qualifications

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

EEO Statement

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