Senior Specialist, Benefits

Checkout.com•Atlanta, GA

8d•Hybrid

About The Position

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. 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!

Requirements

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.

Nice To Haves

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

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 stirategy. 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.