WellSense Executive Team and Board of Trustees

Heather Thiltgen

Heather Thiltgen, President

Heather leads and directs the overall financial and administrative operations of WellSense Health Plan. She works closely with state and federal government entities, regulatory groups, healthcare providers and other external agencies to address the medical and social needs of our membership. Previously, Heather served as senior vice president of Strategic Markets for Medical Mutual of Ohio, one of the state’s oldest and largest health insurers. In that role, she oversaw all product lines, which drove over $1.2 billion in annualized premiums. In addition, Heather launched the company’s Medicare Advantage program in 2016, the largest new plan entrant nationwide that year. Previous to that she held senior leadership positions at CUNA Mutual Group, United Services Automobile Association, and the M/A/R/C® Group. Heather received her Bachelor of Arts from the University of Texas at Austin, and her Master of Business Administration from Vanderbilt University.

Craig Bennett

Craig Bennett, Vice President and Chief Compliance Officer

Craig provides leadership for Boston Medical Center Health Systems' enterprise-wide Compliance program that includes oversight for Privacy, Billing, Pharmacy 340B, and Research and Conflict of Interest oversight for Boston Medical Center, WellSense Health Plan, and Boston University Medical Group. Prior to joining, Craig served as Vice President, Chief Compliance and Privacy Officer at Lahey Health System, a nonprofit, integrated healthcare delivery system. Craig also served as director of Corporate Compliance at Beth Israel Deaconess Medical Center, and director of Compliance and privacy officer at Boston Children’s Hospital, both nonprofit teaching and research hospitals. Additionally, he is a senior lecturer at Northeastern University in Boston and teaches courses in healthcare policy and health law.

Jim-CollinsJim-CollinsJim Collins, Chief Financial Officer

Jim joined WellSense as Chief Financial Officer in December of 2019. Previously, Jim was chief financial officer at DentaQuest/Delta Dental of Massachusetts for eight years where he was in charge of finance, corporate strategy, and data analytics. In addition, Jim brings more than 20 years of financial management experience in insurance and financial services with prior roles including vice president, Financial Analysis and Management Reporting at Sun Life Financial and vice president, Office of the Chief Executive at John Hancock Financial Services. Jim is a Fellow of the Society of Actuaries and received his Bachelor of Arts from Dartmouth College.


Diana (Dee) Cruz, Chief Operating Officer

Diana (Dee) Cruz joined WellSense in 2021 as the Chief Operating Officer. Dee is responsible for improving end-to-end operational processes that drive a better member experience. Prior to joining WellSense, Dee initiated the Office of Consumer Obsession at Cambia Health Solutions, where she employed human-centered design/lean methods and sponsored enterprise programs focused on reducing consumer effort and healthcare costs for members. As vice president of operations at Regence Blue Cross Blue Shield, Dee oversaw improved automation and data science-enabled payment-integrity programs focused on reducing provider and member abrasion. Dee has also held leadership roles at Cigna, in finance, operations, network architecture, and operating effectiveness. Dee received her bachelor’s degree in International Relations from Stanford University and is a Six Sigma Black Belt.

Kim4869Kim Sinclair, Chief Information Officer
Kim, who has been with WellSense since 2002, is responsible for providing leadership and strategic direction for the organization’s Information Technology division. She represents WellSense in government and industry IT forums in which healthcare-related topics are discussed and strategies defined. She is a key contributor to implementing and managing Medicaid and government programs, including national healthcare reform under the Affordable Care Act. Kim is a graduate of Providence College.


Weinstein-7.25.22Ellen Weinstein, Chief Legal Officer
Ellen provides counsel to help WellSense achieve its ambitious vision for the members and communities we serve. She leads a team of lawyers charged with protecting the organization’s legal interests and advancing its business objectives. Ellen is responsible for all legal matters including corporate governance, regulatory affairs, contracting and transactions, and dispute resolution. She has been with Boston Medical Center Health System since 2008. Ellen received her Bachelor of Arts from Yale University, her J.D. from Harvard Law School, and completed a fellowship in medical ethics at Harvard Medical School.


Board of Trustees

  • David Ament, Managing Partner, Parthenon Capital Partners
  • Alastair Bell, Executive Vice President and COO, BMC Health System
  • James Blue, President, Alera Group
  • Stacy Cowan, CEO, SLC Advisory Services
  • Christopher Gordon, Managing Director, Bain Capital
  • Susan Levine, Managing Director, Bain Capital
  • Paul Mendis, MD, Former CMO, Neighborhood Health Plan
  • Jeffrey Schwartz, Managing Director, Bain Capital
  • Robert Sweet, Jr., Retired Partner, Foley Hoag
  • Mark Taber, Managing Partner, Great Hill Partners
  • Heather Thiltgen, President, WellSense Health Plan
  • Kate Walsh, President and CEO, Boston Medical Center Health System
  • Tarsha Weaver, COO, Codman Square Health Center