Ilenna J. Stein is an attorney in Holland & Knight's Boston office, and she is a member of the firm's Healthcare & Life Sciences Team. She also serves as co-chair of the firm's Pharmacy and Prescription Drug Distribution pursuit team. Ms. Stein advises clients in various sectors of the healthcare industry on healthcare regulatory matters, fraud, abuse and compliance matters, and corporate transactional matters.

In particular, she counsels pharmaceutical manufacturers, medical and dental device manufacturers, pharmacies (retail, specialty, long-term care, mail order and compounding), pharmacy benefits managers, dialysis companies, physician groups, home health agencies, private duty companies, healthcare technology companies, insurers and wholesale drug distributors. Specifically, Ms. Stein provides regulatory guidance and advice on matters concerning compliance with the federal Anti-Kickback Statute (AKS), Stark, Medicare, Medicaid, Health Insurance Portability and Accountability Act (HIPAA), Physician Payments Sunshine Act (Sunshine Act), Corporate Practice of Medicine (CPOM), and other federal and state healthcare laws. Ms. Stein also has experience assisting clients in drafting policies and procedures as well as in implementing compliance programs.

Ms. Stein advises clients in a variety of corporate and contractual healthcare transactions, including mergers and acquisitions, licensing matters and structuring transactions. Ms. Stein directly represents buyers and sellers in corporate transactions and advises private equity firms investing in the healthcare space. In addition, she counsels insurers and lenders underwriting representation and warranty (R&W) insurance or loaning funds, respectively, in connection with healthcare transactions. She also has experience handling, responding to, and successfully appealing Medicare and state Medicaid payment audits, as well as HIPAA investigations by the Office for Civil Rights (OCR). In addition, Ms. Stein provides healthcare regulatory advice to educational clients, such as colleges and independent schools, on matters concerning healthcare.

Ms. Stein is the co-chair of the Diversity Committee at Holland & Knight's Boston office.


  • Suffolk University Law School, J.D., Health & Biomedical Law, magna cum laude
  • Tufts University, B.A., Community Health and American Studies, magna cum laude
Bar Admissions/Licenses
  • Massachusetts
  • YW Boston, Lead Boston Program Class of 2022
  • American Health Lawyers Association
  • American Bar Association, Health Law Section
  • Boston Bar Association
Honors & Awards
  • Holland & Knight Rising Star, Class of 2024
  • Rising Star, Health Care, Law360, 2023
  • Top Lawyer, Health Care Law, Boston Magazine, 2022
  • Suffolk University Law School Health & Biomedical Law Concentration Certificate Awarded with Distinction
  • Journal of Health & Biomedical Law, Editor-in-Chief
  • Tufts University Highest Thesis Honors
  • Suffolk University Law School Jurisprudence Awards in Evidence and Professional Responsibility
  • Suffolk University Law School First Year Best Brief & Distinguished Oral Advocate Awards