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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 benefits strategy with operational execution and compliance management.
Key Responsibilities:
- Develop and execute company-wide benefits strategy aligned with competitive labor market positioning and company growth
- Design and modify benefit plans based on market trends and employee needs
- Own annual Open Enrollment strategy, communications, and execution
- Oversee all leave and PTO programs (FMLA, ADA, state leaves, company-specific programs) at scale, including return-to-work coordination
- Manage relationships with leave vendors, TPAs, benefit carriers, brokers, and consultants
- Ensure compliance with federal and state regulations (ERISA, HIPAA, COBRA, FMLA, ADA, ACA)
- Own 401(k) governance, Form 5500 reporting, and compliance testing
- Manage self-insured health and welfare plan budgets, funding, stop-loss, and claims analysis
- Identify and implement AI and automation opportunities to streamline benefits administration and reduce manual work
- Lead, develop, and coach a team of four benefits professionals
- Serve as primary financial steward and interface with Finance on plan costs and allocations
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
- Deep expertise in ERISA, HIPAA, COBRA, FMLA, ADA, ACA, and state/federal benefits law
- Proven leadership experience managing and developing teams
- Strategic yet hands-on leadership style; comfort with both strategy and operational details
- Strong financial acumen and experience with HRIS systems (Workday preferred)
- Advanced Excel and reporting skills
- Experience leveraging AI and automation to transform HR and benefits workflows
- 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 role requires 4 days in-office at Chicago headquarters to foster collaboration and culture.
