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Employee Benefits Associate

Direct Counsel
Chicago, IL Full Time
POSTED ON 6/2/2026
AVAILABLE BEFORE 8/2/2026
Direct Counsel is seeking an Employee Benefits Associate with 1–4 years of experience to join a premier Employee Benefits and ERISA practice. This is an outstanding opportunity for attorneys interested in advising clients on complex employee benefits, retirement plans, healthcare compliance, and benefits-related aspects of corporate transactions and restructurings.

The ideal candidate will have experience with ERISA and employee benefits matters and a strong interest in developing deep subject matter expertise in this highly specialized and growing area of law.

Responsibilities

  • Advise clients on ERISA and employee benefits compliance matters
  • Counsel employers regarding qualified retirement plans, multiemployer pension plans, health and welfare plans, and Affordable Care Act (ACA) requirements
  • Support mergers, acquisitions, private equity transactions, restructurings, and other corporate transactions involving employee benefits issues
  • Conduct benefits-related due diligence and assist with transaction structuring
  • Analyze and advise on retirement plan, healthcare, and employee benefit compliance matters
  • Draft and review benefits-related plan documents, agreements, and compliance materials
  • Collaborate with attorneys across corporate, tax, labor, restructuring, and executive compensation practices

Qualifications

  • 1–4 years of experience in ERISA, employee benefits, tax, labor and employment, or related practice areas
  • Experience with qualified plans, multiemployer pension plans, health and welfare plans, and ACA compliance preferred
  • M&A and/or restructuring experience involving employee benefits issues is strongly preferred
  • Background in related areas such as tax, labor, benefits consulting, or accounting will be considered
  • Executive compensation experience is helpful but not required
  • Excellent analytical, research, drafting, and communication skills
  • Outstanding academic credentials and attention to detail

Compensation & Benefits

  • Base salary range: $225,000 – $310,000
  • Competitive bonus opportunities
  • Comprehensive health and wellness benefits
  • Retirement and savings plan options
  • Opportunity to work alongside leading ERISA and employee benefits attorneys on sophisticated transactional and compliance matters

This opportunity offers exceptional training, mentorship, and the ability to develop specialized expertise in one of the most technically sophisticated and in-demand areas of legal practice.

Qualified candidates are encouraged to apply through Direct Counsel.

Salary : $225,000 - $310,000

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