Director, Benefits

About the role

The real world is the next frontier, and at Metropolis, we are creating the artificial intelligence to make it responsive. We are pioneering the Recognition Economy - a future where mundane repetition disappears and being known unlocks access, comfort, and belonging everywhere you go. From transforming parking into a seamless drive-in, drive-out experience for millions of Members to expanding our intelligence layer across retail and hospitality, we are building a world that feels instinctive and magical. The future isn't coming; it's here, and we need builders, innovators, and problem solvers to help us create it.

Responsibilities

• Set a company-wide benefits strategy with near- and long-term goals that keeps Metropolis competitive, designing new plans and modifying existing ones based on current and future trends
• Identify opportunities to leverage AI and automation to streamline benefits, leave, and PTO processes while reducing manual work
• Own the annual Open Enrollment strategy and ensure benefits communications are accurate, clear, and compelling
• Oversee the strategy, administration, and compliant tracking of all leave and PTO programs across the 20,000+ population, including return-to-work coordination
• Manage leave vendor and TPA relationships while integrating leave and PTO data across HRIS, payroll, and benefit systems
• Hold accountability for compliance with federal and state benefits and leave laws, including ERISA, HIPAA, COBRA, FMLA, ADA, and AC
• Own 401(k) governance and oversee Form 5500 reporting, compliance testing, and required CMS, GAG, and RxDC filings
• Own plan budgets and financial stewardship of self-insured health and welfare plans, serving as the primary interface with Finance to maintain cost-allocation standards
• Act as the senior relationship owner with benefit carriers, brokers, consultants, and TPAs to drive streamlined processes that reduce cost and risk
• Lead, develop, and hands-on coach a team of four by setting clear expectations, ruthlessly prioritizing demands, and removing barriers

Requirements

• 10+ years in benefits administration, including strategy, open enrollment, compliance, and financial/accounting responsibility
• Experience managing self-insured or self-funded health and welfare plans, including funding, stop-loss, and claims or reserve analysis
• Strategic yet hands-on leadership style, staying comfortable in the weeds and willing to do the work alongside the team
• Experience overseeing leave, absence, and PTO programs like FMLA, ADA, state, and company leaves at scale
• Track record of leveraging AI and automation to streamline and scale HR and benefits processes
• Proven leadership experience directing and developing a team, ideally through other managers
• Extensive expertise in ERISA, HIPAA, COBRA, FMLA, ADA, ACA, and applicable state and federal benefits and leave law
• Ability to thrive in a fast-paced, high-growth, tech-forward environment with shifting priorities and a builder's bias for action
• Strong financial acumen, experience administering plans in an HRIS, advanced reporting and Excel skills, and excellent communication abilities
• Familiarity with HRIS systems like Workday

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