Director of Benefits, Metropolis
$175-195k
4+ days a week in office
Autonomous commerce platform for urban mobility
Be an early applicant
Autonomous commerce platform for urban mobility
1001+ employees
Be an early applicant
$175-195k
4+ days a week in office
1001+ employees
Company mission
To disrupt traditional city infrastructure to empower the future of urban mobility.
Role
Who you are
- 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
What the job involves
- 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
Our take
Driven by computer vision and AI technology, Metropolis offers a seamless parking and checkout experience by turning cars into wallets. This eliminates the need for physical tickets and pay machines, allowing property owners to maximise the financial performance of their parking assets and offer a modern service to customers.
Metropolis aims to revolutionise parking by integrating future mobility solutions, such as autonomous vehicle deployment, charging stations, and eVTOL infrastructure. Its approach includes dynamic pricing to optimise revenue during demand surges.
The company has expanded rapidly following several fundraising rounds and some lucrative partnerships. Its acquisition of SP Plus Corporation helped to position Metropolis as a leader in AI infrastructure for parking and mobility, and its now grown to be worth $5 billion.
Steph
Company Specialist at Welcome to the Jungle
Insights
7% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Nov 2025
$500m
SERIES D
Oct 2023
$1.1bn
SERIES C
Total funding: $1.8bn
Company benefits
- Equity options - We offer ownership opportunities through stock options
- Wellness benefits - A wellness program designed to support a variety of needs
- Health insurance - We subsidise high-quality health insurance coverage for full-time and hourly employees
- We subsidize high-quality health insurance coverage for full-time and hourly employees
- 401(k) match - Plan for your future with a 4% company match
- Parental leave - Receive support prior to, during leave, and as you transition back to work
- Time off - Unlimited PTO for salaried employees, and a generous PTO package for our hourly employees
- Paid holidays - We observe major holidays with company-wide closures, and double hourly rates for those who work
- Hybrid environment - Magic happens face to face, but we support a flexible working model
Company HQ
Downtown, Santa Monica, CA
Leadership
Alexander Israel
(CEO & Co-Founder)Former Vice President & General Manager at INRIX. Co-founder and former COO at ParkMe. BA in Business & Economics at University of Puget Sound.
Travis Kell
(CSO & Co-Founder)Former Senior Vice President at Winton Group. Previously Director of Hedge Fund Solutions at BlackRock. BA in Business at University of Puget Sound.
Courtney Fukuda
(Chief Integration Officer & Co-Founder)Formerly hedge fund solutions group at BlackRock. Managed senior relationships with sovereign wealth fund, central banks and other major institutional investors. BA in Economics at Yale University.
Peter Fisher
(CCO & Co-Founder)Formerly growth equity Investor at Transamerica Investment Management, BA in Political Science at Boston College.
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