A seasoned healthcare law attorney who saw first-hand the practical and systemic challenges faced by providers and patients alike well before embarking on her legal career, Cassie Paolillo delivers actionable guidance and pragmatic counsel to clients across the industry on a wide range of transactional and regulatory matters.

Overview

Cassie’s determination to leverage the law as a facilitator of client goals rather than an impediment to them, as well as her creative yet prudent approach to managing compliance and other risks, have made her a trusted strategic advisor for providers, payors, healthcare vendors and a range of investors in the healthcare space. She merges her appreciation of the on-the-ground realities of healthcare with an equally robust understanding of the complex and ever-changing web of laws, regulations and policies that govern the industry and directly impact clinical, operational and financial decision-making.

Collaborative by nature, Cassie works closely with clients, their internal constituencies and interdisciplinary teams to guide them with clarity through the regulatory thicket involved in strategic healthcare transactions, mergers and acquisitions, financing and investment, commercial contracting and other consequential matters. She assists clients with establishing and implementing MSO-PC arrangements, has served as regulatory counsel to various institutional lenders on financing transactions related to the acquisition of health and life science industry companies, and has handled private equity investments in pediatric, dental, ambulatory surgery and addiction treatment providers.

Calm under pressure and clear-eyed and candid in her counsel, Cassie advises clients on HIPAA/privacy compliance, telehealth and other digital health matters, corporate practice issues, professional and facility licensing, determinations of need/certificates of need, and Medicare and Medicaid compliance. Her experience also extends to advising nonprofit organizations on matters related to formation and corporate governance.

Growing up with parents who were healthcare providers and working in hospitals while in college, Cassie listened to and observed the frustrations and rewards, as well as the opportunities and disparities involved in delivering quality care. If not preordained, practicing healthcare law was certainly a natural calling for Cassie. Having served as in-house counsel at a national senior living company before moving to private practice, Cassie also intuitively recognizes what healthcare clients need from their outside counsel and works tirelessly to protect their interests and help achieve their goals.

Cassie’s passion for healthcare, particularly in addressing health disparities, extends beyond her work for clients to her active pro bono practice, which focuses on increasing access to reproductive healthcare and behavioral health services, including substance use disorder treatment. She serves on the board of the South Boston Collaborative Center, a substance abuse and mental health treatment center located in South Boston.

Representative Matters
  • Served as lead regulatory counsel to a publicly traded clinical laboratory in its acquisition of another laboratory, including coordinating pre-transaction review filings in California, Indiana, Massachusetts and Oregon.
  • Served as lead deal and regulatory counsel on a number of joint ventures for a national ambulatory surgery provider.
  • Advised telehealth start-up serving the LGBTQ+ community in developing and executing a 50-state regulatory and operational strategy.
  • Advised a large academic medical center on its AI governance structure, including participating in the organization’s AI risk assessment and governance committee.
  • Served as lead regulatory counsel on a physician practice acquisition, successfully representing one of Massachusetts’ largest community-based medical practices before the Massachusetts health policy commission.
  • Served as Massachusetts Determination of Need (“DON”) counsel for several national healthcare providers.
  • Assisted behavioral telehealth company aimed at addressing the needs of acute care providers in streamlining its customer contracting process.
Credentials

Education
Boston College, B.S., English, Irish Studies minor, 2009
Suffolk University Law School, J.D., Health and Biomedical Law Concentration with Distinction, 2014

Bar Admissions
Massachusetts, 2014

Noteworthy
  • Best Lawyers in America: Ones to Watch – Health Care Law (2024 – 2026)
  • Recognized by The Legal 500 United States for Healthcare: Service Providers (2025)
  • Massachusetts Super Lawyers Rising Stars: Health Care (2022 – 2024)
  • Massachusetts Lawyers Weekly: Up & Coming Lawyer (2024)
Community Involvement
  • American Health Lawyers Association, member
  • American Telemedicine Association, member
  • Chuhak & Tecson’s Women Helping Women Program, ambassador
  • Class of 2022, Greater Boston Chamber of Commerce Women’s Leadership Program
  • South Boston Collaborative Center, board member
Lectures/Speaking Engagements
  • 2026 Journal of Health & Biomedical Law Symposium, Suffolk University Law School, Boston, MA
  • Boston Bar Association Health Law Section Event, Boston, MA
  • 2024 BCBS Law, Audit, Compliance & Ethics Conference, Nashville, TN
  • Women Business Leaders of the U.S. Health Care Industry Foundation, Webinar