Benefits Administrator

At WIN Brands (encompassing Costa Vida and FatCats locations), we believe our benefits should do more than protect our employees—they should reflect who we are: a values-driven organization committed to excellence, empathy, and integrity. We’re looking for a Benefits Administrator who brings solid experience in benefits administration and a desire to grow into a subject matter expert. This individual will manage the day-to-day operations, vendor partnerships, policy administration, and compliance functions that support our benefits programs.

This role is ideal for someone who enjoys working independently, improving processes, and providing meaningful support to internal teams. The Benefits Administrator will serve as a critical partner to HR, Payroll, and Finance—ensuring accuracy, efficiency, and an exceptional employee experience.

This is a process-focused role and requires someone with strong follow-through, attention to detail, and a mindset of continuous learning and ownership.

• Oversee the daily administration of all benefit programs, including health, dental, vision, life insurance, disability, wellness, FSA/HSA, and 401(k).
• Serve as a liaison for benefits vendors and third-party administrators (TPAs), managing issue resolution, file feeds, renewals, and performance metrics.
• Coordinate and execute the full annual Open Enrollment process, including system setup, employee communications, testing, and post-enrollment audits.
• Manage benefits eligibility events such as new hires, terminations, life events, COBRA notices, and leaves of absence.
• Maintain compliance documentation and internal procedures, ensuring accuracy of Summary Plan Descriptions (SPDs), SBCs, and policy resources.
• Ensure benefits programs comply with ACA, ERISA, HIPAA, COBRA, FMLA, ADA, IRC Section 125, and DOL guidelines.
• Prepare for and support compliance activities including 5500 filings, non-discrimination testing (NDT), 401(k) audits, and dependent eligibility audits.
• Reconcile benefit invoices and payroll deductions; partner with Payroll and Finance to resolve discrepancies and maintain audit-readiness.
• Create and organize employee-facing resources such as benefit guides, FAQs, and training materials; support onboarding and open enrollment communications.
• Deliver responsive and confidential support for employee benefits questions and complex case resolutions.

Qualifications & Skills

• Bachelor’s degree in Human Resources, Business Administration, or related field. Preferred. 
• Demonstrated progressive experience in U.S. benefits administration.
• Understanding of relevant federal and state benefits regulations (ACA, ERISA, HIPAA, COBRA, FMLA, ADA, DOL, IRS Section 125).
• Proficient with HRIS systems, preferably Paylocity, and benefits administration platforms.
• Excellent written and verbal communication skills; capable of simplifying complex topics for diverse audiences.
• Self-motivated and able to operate with minimal direction while maintaining high accountability.
• Preferred certifications: CEBS, SHRM-SCP, SPHR.

Core Competencies

• Compliance-Driven – Maintains up-to-date understanding of regulations and ensures operational adherence.
• Service-Oriented – Prioritizes clear, compassionate support for employees and team partners.
• Collaborative Partner – Works cross-functionally to deliver seamless benefits administration.
• Detail-Focused – Accurately manages complex processes, data, and documentation.