Director, Benefits

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 corporate team members hold to our office-first model, which requires employees to be on-site at least four days a week, fostering organic interactions that spark creativity and connection.

When you join Metropolis, you'll join a team of world-class product leaders and engineers, building an ecosystem of technologies at the intersection of parking, mobility, and real estate. Our goal is to build an inclusive culture where everyone has a voice and the best idea wins. You will play a key role in building and maintaining this culture as our organization grows. The anticipated base salary for this position is $175,000.00 USD to $195,000.00 USD annually. The actual base salary offered is determined by a number of variables, including, as appropriate, the applicant's qualifications for the position, years of relevant experience, distinctive skills, level of education attained, certifications or other professional licenses held, and the location of residence and/or place of employment. Base salary is one component of Metropolis' total compensation package, which may also include access to or eligibility for healthcare benefits, a 401(k) plan, short-term and long-term disability coverage, basic life insurance, a lucrative stock option plan, bonus plans, and more. #LI-AW1 #LI-Onsite