Leadership team

Drew DiGiorgio

President & CEO

As President & CEO of Wellfleet, Drew DiGiorgio is driving expansion and diversification of product offerings by providing unique health care solutions that improve the quality of care while maintaining profitability.

Brad Newell

Chief Financial Officer

Executive VP, Strategy

Brad oversees all Finance and Strategy functions within Wellfleet. His core responsibilities include Accounting, Actuarial, Planning & Analysis, and Underwriting.

Karen Matys

Chief Operating Officer

Karen has more than 20 years experience in the healthcare industry. In her role at Wellfleet, Karen is responsible for Claims, Customer Service, Support Services, Enrollment, Waiver and Insurance Administration.

James Ocampo

EVP, Workplace BenefitS

James was hired in 2018 to lead Wellfleet’s venture into the workplace benefits space. Most recently MassMutual’s VP, Worksite Insurance, James carries extensive experience in technology, strategy, and business development.

Phil LaCombe

Chief Information Officer

Phil has more than 20 years of IT experience combined with more than 10 as a leader in business operations. He is skilled and demonstrates core competencies in Executive, IT and Leadership areas.

Dr. Barrie Baker

Chief Medical Officer

Barrie Baker, MD, MBA is a Board-Certified Family Practitioner with 10 years’ clinical experience and more than 15 years of experience in Managed Care administration. Barrie oversees clinical policy and decision making, pharmacy, and network management.

Aaron Krieger

Chief Legal Officer

Aaron has over a decade of in-house legal experience in the insurance industry. Aaron oversees the Legal Department, which includes the Legal, Compliance, Filing, Appeals and Licensing & Appointment teams.

Juan Campbell


& Client relations

Juan manages sales, operations, strategic marketing and business development strategies for Wellfleet’s College & Special Risk segment, utilizing his 20-plus years of experience in health insurance.

Jay Fearrington



Jay’s background combines many years in executive roles focused on project management, business development, account management, and sales in industries ranging from IT, Insurance to Manufacturing. 

Ben Larsen

Director of Marketing

& Communications

Ben oversees Wellfleet’s marketing and communications, including all brand, advertising, and content. He also drives leadership in digital experience, including user experience and digital product management.

1500 Main Street, Suite 1000, Springfield, MA 01115-5369

Wellfleet is the marketing name used to refer to the insurance and administrative operations of Wellfleet Insurance Company, Wellfleet New York Insurance Company, and Wellfleet Group, LLC. All insurance products are administered or managed by Wellfleet Group, LLC. Product availability is based upon business and/or regulatory approval and may differ among companies. ©2023 Wellfleet Group, LLC. All Rights Reserved.