Director, Regulatory Compliance Specialist, Management

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.

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.

• 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

• 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
• Experience leveraging AI tools to transform static workflows into responsive, high‑output processes.

4 Days in Office: Metropolis values in‑person collaboration to drive innovation, strengthen culture, and enhance the Member experience. Our…