Director, Benefits

About the Company

Metropolis is creating the artificial intelligence to make the real world responsive. We are pioneering the Recognition Economy, transforming parking and expanding our intelligence layer across retail and hospitality to build a world that feels instinctive and magical.

Responsibilities

• Set company-wide benefits strategy with near- and long-term goals to maintain competitiveness
• Identify opportunities to leverage AI and automation to streamline benefits, leave, and PTO processes
• Own the annual Open Enrollment strategy and ensure clear, compelling communications
• Oversee strategy, administration, and compliant tracking of all leave and PTO programs
• Manage leave vendor and TPA relationships and integrate data across HRIS, payroll, and benefit systems
• Ensure compliance with federal and state laws including ERISA, HIPAA, COBRA, FMLA, ADA, and ACA
• Own 401(k) governance, Form 5500 reporting, and required filings
• Manage plan budgets and financial stewardship of self-insured health and welfare plans
• Act as senior relationship owner with benefit carriers, brokers, consultants, and TPAs
• Lead, develop, and coach a dedicated team of four

Requirements

• 10+ years in benefits administration including strategy, compliance, and financial responsibility
• Experience managing self-insured or self-funded health and welfare plans
• Experience overseeing leave, absence, and PTO programs at scale
• Track record of leveraging AI and automation to scale HR processes
• Proven leadership experience directing and developing a team
• Extensive expertise in ERISA, HIPAA, COBRA, FMLA, ADA, and ACA
• Strong financial acumen and advanced Excel skills
• Familiarity with HRIS systems such as Workday