Checkout.com · 2 hours ago
Senior Specialist, Benefits
Atlanta, GA
Full-time
Onsite
Senior Level
5+ years expCheckout.com is a global payments company that powers billions of transactions every year. They are seeking a proactive Benefits SME to design, implement, and enhance benefits programs across the Americas, focusing on strategic planning, vendor management, and operational excellence.
FinTechPaymentsTransaction Processing
Responsibilities
Lead Benefits Administration: You'll own and execute the day-to-day operations of our regional benefits programs across the Americas. 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. You'll also be responsible for 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. 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, independently managing the full scope of benefits for the Americas while ensuring both operational excellence and long-term strategic enhancements
Qualification
Required
5+ years of Benefits Expertise: Extensive experience managing end-to-end benefits programs, with a deep understanding of benefits strategy, design, and administration for the US and Canada. Experience with benefits 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. Strong knowledge of US FMLA and leave administration in a multi-state environment, as well as Workers' Compensation, IRS, and ERISA regulations
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, including launching Open Enrollment, updating benefit plans, and running reports
Preferred
Experience in a fast-paced, high-growth technology or FinTech environment
Professional certifications (e.g., CEBS, PHR/SPHR)
Fluency in Spanish
Fluency in Portuguese
Benefits
Flexibility, with three days per week in the office to support collaboration and connection.
Company
Checkout.com
Checkout.com is a global provider of payment solutions that help businesses and communities thrive in the digital economy.
1001-5000 employees
Funding
Current Stage
Late StageTotal Funding
$1.83BKey Investors
Tiger Global ManagementCoatue
2022-01-12Series D· $1B
2021-01-11Series C· $450M
2020-06-22Series B· $150M
Leadership Team
Guillaume Pousaz
Founder & CEO
Mariano Albera
Chief Technology Officer
Recent News
2026-01-20
Financial Sector Technology
2026-01-16
2026-01-16
Company data provided by crunchbase