Who We Are

Building Methodical, meaningful relationships

OUR HISTORY

Matthew Naylor founded Crumdale Partners in 2014 with a goal to fix the broken healthcare supply chain and create innovative insurance solutions for better self-funded employee benefits.

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 FOUNDATION

Methodical, meaningful relationships between broker partners and trading partners.

OUR MOTIVATION

To revolutionize employee benefits through market-leading products and services.

OUR COMMITMENT

To provide strategic consulting, innovative solutions, and impactful partnerships.

“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, trading partners, 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

Matt 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.

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Brian J. McTear

PRESIDENT

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

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Jake Willcox

EXECUTIVE VICE PRESIDENT

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. 

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Joseph C. Sweeney

CHIEF OPERATING 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.

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Robert S. Adams

CHIEF FINANCIAL OFFICER

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.

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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. 

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