Manager, Heath and Benefits Administration

About the Role

Gap Inc. is seeking a strategic, detail-driven, and customer-focused leader to join our Total Rewards team as Manager of Health & Benefits Administration. In this pivotal role, you’ll lead the day-to-day operations and ongoing evolution of our healthcare programs, supporting our vision to become a high-performing house of iconic American brands that shape culture.

This role oversees the full suite of Gap Inc. health and benefits offerings—including medical, prescription drug, dental, and vision coverage—for more than 25,000 eligible employees across the U.S. and Canada. With a mindset rooted in curiosity and accountability, you’ll help ensure our plans operate smoothly, meet compliance standards, and deliver a transparent, inclusive, and accessible experience. Vendor relationships, process improvements, and support for global initiatives as needed also fall within your remit.

Success in this role requires pairing operational excellence with a deep commitment to enhancing the employee experience—so every interaction with our healthcare benefits is service-driven, supportive, and meaningful.

What You'll Do

• Champion an inclusive and accessible employee experience across all healthcare benefit programs and touchpoints

• Oversee daily administration of U.S. and Canadian healthcare benefits—including insured and self-insured plans—ensuring accuracy, compliance, and seamless access to care

• Lead Open Enrollment and year-round campaigns, including planning, testing, communications, and employee support

• Develop and deliver educational healthcare communications such as webinars, Q&A sessions, and benefit guides to empower informed decision-making

• Manage relationships with healthcare carriers, TPAs, brokers, and technology vendors to ensure high-quality service and member satisfaction

• Collaborate with Finance and consultants on plan renewals, updates, and performance analysis; monitor feedback and service data to improve employee experience

• Partner with Payroll, HR Technology, and Finance to ensure accurate eligibility, payroll deductions, and funding processes

• Maintain plan documents, SPDs, benefit summaries, and compliance deliverables; ensure adherence to U.S. and Canadian regulatory requirements

• Act as Tier 3 escalation contact for complex healthcare benefit inquiries, resolving issues with empathy and efficiency

• People leader for Senior Benefits Analyst while supporting global benefits initiatives and sharing best practices across regions

Who You Are

• Proven success managing U.S healthcare benefit programs for national employers, with familiarity across self-insured and HMO plan structures

• Experience with or strong aptitude/willingness to learn managing Canadian healthcare benefits across multiple provinces

• Skilled in vendor management and issue resolution, ensuring high-quality service delivery and member satisfaction

• Solid understanding of regulatory requirements including ACA, ERISA, HIPAA, COBRA, and applicable state and provincial laws

• Demonstrated ability to handle escalated employee benefit inquiries with empathy and efficiency

• Proficient in HRIS and benefits administration platforms; advanced Excel skills for data analysis and reporting

• Able to create and edit employee-facing materials in MS Word and PowerPoint to support engagement and education

• 7+ years of hands-on experience administering health and welfare benefits, including medical, prescription drug, dental, and vision plans