Employee Benefits Attorney – Chicago or Milwaukee

Locations: Chicago, IL | Milwaukee, WI

Our client, a prestigious AmLaw 50 law firm, is seeking a talented Associate Attorney to join its Health Benefits Practice. This position is part of the broader Employee Benefits & Executive Compensation Practice Group and can be structured as either a partner-track or non-partner-track role, depending on the candidate’s interests and background. The primary office locations for this opportunity are Chicago and Milwaukee, though candidates in other cities may be considered based on qualifications and business needs.

Candidate Profile:

• JD from an ABA-approved law school with a strong academic record.

• Active Bar Admission in the relevant jurisdiction.

• 1–8 years of substantive experience in employee benefits law, with a focus on ERISA health and welfare benefits, health insurance compliance, or third-party administrator regulatory matters.

• Demonstrated experience advising TPAs, PBMs, HRA vendors, and other service providers in the health plan space, or counseling employers on compliance with health plan-related laws such as HIPAA, the ACA, the No Surprises Act, mental health parity regulations, wellness programs, or cafeteria plans.

• Ability to distill and communicate complex legal concepts clearly—ranging from regulatory contracts to simplified summaries for general audiences.

• Strong research, analytical, drafting, and communication skills.

• A proactive, team-oriented mindset, with high attention to detail and the ability to manage multiple assignments in a fast-evolving legal landscape.

Key Responsibilities:

• Advise a diverse client base—including employers, third-party administrators, insurers, and vendors—on ERISA and health benefit compliance issues.

• Provide strategic guidance in response to evolving legislation, litigation, and regulatory updates impacting the health and welfare benefits landscape.

• Draft and review service provider agreements, plan documents, compliance materials, and client-facing summaries.

• Conduct legal research and prepare memoranda on HIPAA, the ACA, mental health parity, the No Surprises Act, HSA requirements, and related topics.

• Collaborate with attorneys across the firm on interdisciplinary matters involving regulatory, transactional, and litigation support for benefit-related issues.

Why Join Us?

This is not just a job–this is an exciting opportunity to develop deep expertise in one of the most legally and politically active areas of employee benefits law. You’ll work with a team that combines cutting-edge legal work with a client-focused, collaborative culture. Attorneys here enjoy high levels of responsibility, mentorship from nationally respected partners, and the chance to engage directly with industry-leading clients. Whether you’re early in your career or looking to refine a specialized practice, this role offers meaningful growth, professional autonomy, and the support of a firm that values its people as much as its work.

The firm provides competitive compensation, commensurate with experience, along with a comprehensive benefits package that includes medical, dental, and vision insurance, 401(k) retirement plans, paid time off, and additional perks.

Application Requirements:

Interested candidates should submit a resume, cover letter indicating office preference, and law school transcript.

Our client is an Affirmative Action/Equal Opportunity Employer.

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Chicago Applicants: Our client offers a comprehensive benefit program which currently includes Medical, Dental and Vision insurance; 401(k) Retirement; Disability and Life insurance; Adoption Assistance; Backup Care for Dependents. Pursuant to the Illinois Equity Pay Act, the expected salary range for this Denver based position is between $225,000 - $390,000. Actual pay will be determined based on experience and other job-related factors permitted by law.