Ryan J. Cuthbertson


“My father is a physician, which has instilled in me an appreciation of the work health care providers do and the challenges they face. I feel fortunate that I am able to use my legal skills and background to support providers and help them achieve their business and professional objectives.”

For health care providers ranging from telehealth start-ups to large hospital systems, Ryan Cuthbertson provides guidance on a wide range of transactional, operational, and compliance matters. He serves as a trusted advisor who establishes the structures, crafts the agreements, and facilitates the deals that position his clients for long-term success.

With experience handling all manner of health care transactions from concept to consummation, Ryan focuses on complex joint ventures, practice acquisitions, and real estate transactions and leasing arrangements.  His transactional work includes regulatory diligence, contract drafting and negotiation, closing, and pre-and post-closing licensing and regulatory (CHOW) issues. He spent ten years as a United States Air Force officer, where he led diverse teams and honed his ability to effectively work with people with different personalities and experiences towards a common objective. 

Ryan’s clients include pharmacies, laboratories, substance abuse treatment facilities, durable medical equipment suppliers, hospital systems, dialysis providers, long-term care facilities, and medical practices. They appreciate Ryan’s responsiveness, down-to-earth demeanor, and practical approach. He regularly advises telehealth start-up companies from a corporate and compliance perspective on structuring and expanding their business models nationally. Ryan also helps health care providers of all kinds with drafting and negotiating contracts with other providers, employees, contractors, vendors, and payors, with a focus on regulatory compliance.

Comprehensive representation for practice acquisitions and real estate transactions forms a substantial part of Ryan’s practice. He drafts and negotiates initial letters of intent, performs regulatory and corporate due diligence, advises on transaction structure based on that diligence, prepares the appropriate transaction documents, assists with changes of ownership related to licensure and certification, and Medicare/Medicaid enrollment applications. He also helps structure compensation arrangements to reduce risk under fraud and abuse laws.  

Representative Matters

  • Qualified and formed professional entities over two years in 38 states on behalf of a women’s telehealth company initially operating in only three states.
  • Developed employment and services agreements for providers such as Licensed Clinical Social Workers, Psychologists, Physicians, Nurse Practitioners, and Dieticians.
  • Successfully negotiated the acquisition of interests in Medicare Secondary Payor litigation claims for a hedge fund client in a deal that involved holdbacks, waterfall earn-out payments, purchase options, rights of first refusal, and uncommon corporate structures, including a special purpose acquisition company (SPAC) and Delaware Series LLCs. 
  • Assisted with an $8 million purchase of a medical office building from a real estate investment trust.
  • Successfully established multiple medical practices in New York, including navigating a unique and challenging approval process with the New York Department of Education.
  • Handled dozens of regulatory filings in connection with the $35 million acquisition of a multi-state hospital system by a private company, including filings for enrollment, accreditation, and licensing for each facility.
  • Led the acquisition of neighboring properties from local municipalities on behalf of a community hospital, including reviewing survey and underlying survey documents to find title issues, negotiating agreements to mitigate the potential impact of such issues, and closing the transaction on schedule according to the hospital’s development plans.
  • Drafted and negotiated subleases for a medical office building space with medical and dental practices on behalf of a community hospital.
  • Super Lawyers, Massachusetts
  • Health Care, Rising Star, 2019-2023

  • Boston Magazine
  • Top Lawyers - Healthcare Law, 2023

  • CALI Awards: Administrative Law
  • Mediation, Landlord-Tenant Law, and Land Use Law

  • Trustee Academic Scholarship
  • First in Class 2011-2012

  • Academic Achievement Scholarship
  • 4 years

  • New England Scholar
  • Top 10% of class for 4 years

  • Best Lawyers
  • Ones to Watch, Health Care Law, 2024

  • American Health Lawyers Association
  • American Bar Association
  • Chair of the Health Law Section's Website and Technology Committee

  • Boston Bar Association