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.

Betsy Stevens



Betsy Stevens, Esq., joined Wellfleet in 2014 and brings over 23 years of experience in the legal and compliance fields. Her specialties are Legal, Compliance, Regulatory, Self-Insurance, Product Development and Filing, HIPAA and Cybersecurity, Licensing and Corporate Governance, Network/Provider/PBM contracting, and regulatory oversight of Medical Management, Quality and Accreditation. 

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.

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. 

Lindsay Loomis



Lindsay oversees all operations for Wellfleet’s Strategic relationships in the student insurance market. Lindsay has nearly 20 years of experience in operations, health care, and management. 

Juan Campbell

VP, Sales & Marketing

College & Special Risk

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.

PO Box 15369, 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. ©2019 Wellfleet Group, LLC. All Rights Reserved.