Director, Benefits

Who we are 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. Who you are Metropolis is seeking a Director, Benefits to set strategy and own accountability for all company-wide benefit programs across our 20,000+ employees. In this role, you will manage plan funding, claims experience, and financial risk while moving fluidly between leader-ready strategy and the details of a complex claim, compliance filing, or stuck process. You are an energized, hands-on player-coach who thrives in a fast-paced, high-growth environment, biased toward action, and capable of leveraging technology, automation, and AI to scale our People Operations function. Partnering closely with Finance and leading a dedicated team of four, you will build structure, establish continuous compliance, and maintain a competitive edge in the labor market. What you'll do 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 What we're looking for 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 4 Days in Office: Metropolis values in-person c