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Salary: USD 175,000 - 200,000 / annual
Metropolis Technologies is seeking a Director of Benefits to lead all company-wide benefit programs for 20,000+ employees. This is a strategic and hands-on role that combines high-level planning with operational execution.
Key Responsibilities:
- Develop and execute company-wide benefits strategy, including plan design and modifications based on market trends
- Manage annual Open Enrollment strategy and benefits communications
- Oversee all leave and PTO programs (FMLA, ADA, state leaves) at scale, including return-to-work coordination
- Own 401(k) governance, Form 5500 reporting, and compliance testing
- Manage self-insured health and welfare plan budgets and financial stewardship
- Ensure compliance with federal and state regulations (ERISA, HIPAA, COBRA, FMLA, ADA, ACA)
- Lead vendor and TPA relationships with benefit carriers, brokers, and consultants
- Identify opportunities to leverage AI and automation to streamline benefits processes
- Lead, develop, and coach a team of four direct reports
- Partner closely with Finance on cost allocation and plan funding
Required Qualifications:
- 10+ years in benefits administration including strategy, open enrollment, compliance, and financial responsibility
- Experience managing self-insured or self-funded health and welfare plans
- Proven leadership experience directing and developing teams
- Deep expertise in ERISA, HIPAA, COBRA, FMLA, ADA, ACA, and applicable state/federal benefits law
- Experience overseeing leave and absence programs at scale
- Strong financial acumen and advanced Excel skills
- Familiarity with HRIS systems (Workday preferred)
- Track record of leveraging AI and automation to transform HR processes
- Ability to thrive in fast-paced, high-growth, tech-forward environment
Metropolis is an AI company pioneering the Recognition Economy, transforming parking and expanding into retail and hospitality. The company values in-person collaboration with an office-first model requiring four days per week on-site.
