# Director, Benefits

**Company:** [Metropolis](https://hotfix.jobs/companies/metropolis)
**Location:** Chicago, IL
**Role:** People Ops
**Salary:** $175k – $195k/yr
**Experience:** 10+ years
**Skills:** Benefits Administration, Erisa, HIPAA, Cobra, Fmla, Ada, Aca, Workday, HRIS, Self-Insured Health Plans, 401(K) Governance, Open Enrollment, Leave Management, Financial Stewardship, Compliance
**Posted:** 2026-06-23

> Sets company-wide benefits strategy, oversees leave/PTO programs, manages compliance and vendor relationships, and leads a team of four in a fast-paced tech environment. Requires 10+ years of benefits experience and deep expertise in ERISA, HIPAA, FMLA, and self-insured plans.

## Job Description

## What you'll do
- 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 ACA
- 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

## What we're looking for
- 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

## Compensation and Benefits
- Anticipated base salary: $175,000 - $195,000 USD annually
- 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

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