Who We Are
Building Methodical, Meaningful Relationships

Matthew Naylor founded Crumdale Partners in 2014 with a goal to fix the broken healthcare supply chain and create innovative insurance solutions in the self-funded space. Today, we are one of the Inc. 5000 Fastest Growing Companies and consistently ranked among the Best Workplaces. Our enterprise is driven by an entrepreneurial spirit and grounded in meaningful relationships.

Our History

“I founded the company with a true entrepreneurial spirit and a focus on meaningful relationships. Our institutional governance focuses on collaboration and alignment of interests. These interests include our team, our culture, strategic partnerships, vendors, and ultimately our customers. Our vision to make a positive impact on the people we serve is what drives me and what drives our company. Our leadership team has deep-rooted operational experience in a diverse array of insurance solutions, including program management, consulting, risk management, underwriting, cost containment, and analytics. Additionally, private equity expertise and experience drive our company’s mergers and acquisitions and strategic partnerships with a keen eye for success. All these skillsets coalesce within our distributed leadership model under one unified vision to create an innovative, entrepreneurial, team-oriented culture.” – Matthew S. Naylor

Our Leadership

Matthew S. Naylor

Matthew S. Naylor

Founder & CEO


Matthew founded Crumdale Partners with a true entrepreneurial spirit while focusing on governance collaboration and alignment of interests. As CEO, he is responsible for leading Crumdale’ s vision and strategy. He has extensive experience in employee benefits, risk management, MGAs, MGUs, and reinsurance services, as well as related mergers and acquisitions. 

Matthew uses his deep industry expertise along with his distinctive leadership approach to ensure Crumdale delivers exceptional products and services to its clients while continuing to build Crumdale’ s capabilities organically and through acquisition. He has grown multiple industry-related businesses into strong, sustainable entities.

 Matthew began his career in 1995 when he joined Elite, where he built, lead, and acquired MGAs, MGUs, employee benefits, and risk management services across the United States. He sold the business to Houston International Insurance Group in 2015 and became the CEO and President of their Accident and Health Division. He is also a partner and investor in Leverage Health Solutions, an advisory firm to innovative companies in the health insurance payer and provider space, which has generated hundreds of millions in revenue growth for its clients. Matthew was also the lead investor in Health Insurance Inc. (HIIQ) (Nasdaq). He identified, developed, lead, and scaled Health Insurance Inc. to leverage its proprietary technology into the second largest short-term medical insurance distributer in the country.

 Matthew has served on public, private, and nonprofit boards. He is active in the Young President’s Organization (YPO) and a member of YPO International. He has been involved with industry associations, including the Self-Insured Institute of America (SIIA), the Council of Insurance Agents and Brokers (CIAB), the Society of Professional Benefits Administrators (SPBA), and the Society for Human Resource Management (SHRM).

 Matthew received his B.S. from Drexel University and serves as a member of Drexel University Board of Trustees. He is also Chairman of the Board of Trustees for AIM Academy, which is regarded as one of the best academic institutions for learning deficiencies in the United States.

Brian J. McTear

Brian J. McTear


Jake Willcox

Jake Willcox

Executive Vice President


Brian leads Crumdale’s day-to-day operations and the execution of our strategic growth initiatives.

Brian joined Crumdale Partners in 2016. He was previously Senior Vice President at Preferred Sands, a provider of silica sand and technology products to the oil and gas industry, where he was a member of the senior leadership team and had responsibility for new product development, corporate development, and legal matters.

Brian was previously a Partner at Blank Rome, LLP, where he advised public and private companies as well as private equity firms and their portfolio companies on sophisticated business, corporate, and transactional matters.

Brian earned his B.S. in Psychology from Ursinus College and graduated Magna Cum Laude from Widener University School of Law, where he was editor-in-chief of the law review. He has served as a guest lecturer on entrepreneurism at Temple University and Drexel University, has numerous legal publications, and was named to SmartCEO Magazine’s Legal Elite list and recognized as a “Rising Star” by Super Lawyers Magazine. Brian is a member of the Malvern Preparatory School Board of Trustees and is the past Chair of the Bryn Mawr Rehabilitation Hospital Foundation.

Jake leads Crumdale’s global Sales and Marketing strategy. His deep industry experience and leadership in employee benefits and risk management helps ensure the success of Crumdale’s ecosystem.

Jake joined CEO Matt Naylor in 2014 to help launch Crumdale Partners. His vision and passion aligned with the entrepreneurial spirit that Matt brought to bear.

Jake is an active member in Young President’s Organization (YPO) and a member of YPO International. Prior to joining forces with Matt, Jake served in various leadership and sales roles in the insurance industry.

Jake earned his B.A. in International Business from Loyola University where he was a four-year varsity athlete, dean’s list student, and university ambassador. He continues to support the university on various fronts.

Joseph C. Sweeney

Joseph C. Sweeney

Chief Operating Officer

Robert S. Adams

Robert S. Adams

Chief Financial Officer


Joe is Crumdale’s Chief Operating Officer. He has been involved in the insurance industry on the financial and operations side of the business for close to 20 years. During his career, he has served in leadership positions as both the CFO and COO of agencies, insurance carriers, and Managing General Underwriters.

Joe has been involved in numerous acquisitions and divestitures in the insurance space. He prides himself on not only being a part of teams that buy and sell businesses but helping to position those businesses to grow and operate efficiently.

Joe earned his B.S. in Accounting from The Pennsylvania State University and an MBA from Temple University. He is a licensed CPA in the Commonwealth of Pennsylvania.

Rob oversees Crumdale’s financial strategy, accounting, and elements of our agency acquisition process. He has over 20 years of broad investment and financial experience, including venture capital, business strategy development and implementation, financial analysis and modeling, and M&A. Rob has extensive experience in corporate governance, having served on 15 boards of both private and public companies.

Rob is the Founding Partner of NextStage Capital, a seed and early-stage venture fund, where he built a portfolio of 16 technology investments with both equity and debt capital. Before that, he was a Principal and Vice President of Safeguard Scientifics, where he was instrumental in developing numerous technology companies from early-stage through public entity. While there, he sourced, structured, and negotiated over $100M in investments and $380M in mergers, acquisitions, and exits. He began his career in the Entrepreneurial Services division of Ernst & Young.

Rob earned his B.A. in Economics from Skidmore College and an MBA with distinction from the University of Michigan. He is a licensed CPA.

Jim Andrews

Jim Andrews

Chief Revenue Officer


Jim is responsible for training, coaching, and leading Crumdale’s sales team to drive results and revenue. He has extensive experience in sales management at leading payroll and HR companies including Paycheck, Paylocity, and Workday.

Jim leads the execution of Crumdale’s Sales and Marketing initiatives and is intimately involved in recruiting top talent to join the team. Since joining the organization in 2022, he has hired sales leaders across the country, expanding Crumdale products and solutions into new markets.

Jim holds a B.A. from Cabrini University.

Our Solutions

We offer a diverse and integrated set of insurance solutions from a family of partners
with a singular focus and goal. Each partnership is carefully cultivated to creatively
meet real market needs and serve every stakeholder with integrity.

Integrated Health Plans

Pharmacy Solutions


Compliance Services

Actuarial Services


Insurance isn’t new,
but the way we tailor it to meet
your needs is. Contact us today for
a complimentary, confidential client assessment.