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Richard A. Szczebak

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Richard A. Szczebak has more than 30 years of experience as an ERISA benefits lawyer and consultant. He concentrates his practice exclusively in employee benefit compliance matters, including state and federal health care reform. He has helped employers - large and small - implement employee benefit plans and solve problems and issues related to ERISA, COBRA, HIPAA; COVID-19 Relief Compliance; MA Paid Family and Medical Leave; Affordable Care Act Compliance; and much more.

Rick lectures frequently on employee benefit law, health care reform, and related issues. He is well-regarded for his ability to discuss technical issues in a practical manner. His varied experience allows him to consider all perspectives of the compliance spectrum. His career includes service in both a large corporate and a small boutique law firm, a major insurance carrier, a national benefit outsourcing vendor, and a government regulator. RAS Law P.C. brings experience, knowledge, and perspective to your project.



  • Marquette University Law School, Milwaukee, Wisconsin
    • Juris Doctorate
    • Honors: cum laude
  • University of Massachusetts, Amherst, Massachusetts

Past Positions

  • Parker Brown Macaulay & Sheerin, P.C., Of Counsel
  • MA Commonwealth Health Insurance Connector Authority, Legal Advisor
  • MA Division of Health Care Finance and Policy
  • Ropes & Gray LLP
  • Fidelity Investments, Vice President of Health and Welfare Compliance
  • Mass Mutual Life Insurance Company, Counsel

Published Works

  • Bloomberg BNA Tax Management Portfolio on Code Section 125 Cafeteria Plans, Szczebak, 397-4th T.M., Cafeteria Plans, 2020

Practice Areas

  • Affordable Care Act Compliance
  • MA Health Care Reform
  • Health and Welfare Plan Docs/SPDs
  • IRS 226J Penalty responses
  • ERISA compliance audits
  • Section 125 Plans
  • FSAs, HSAs, HRAs and QSEHRAs
  • Employee benefit taxation issues
  • 3rd Party Vendor Contracting
  • 5500 Compliance

Current Employment Position

  • ERISA benefits lawyer and consultant

Bar Admissions

  • Wisconsin, 1985
  • Massachusetts, 1985
  • U.S. District Court District of Massachusetts, 1986
  • U.S. District Court Eastern District of Wisconsin, 1985