Who We Are
Building Methodical, meaningful relationships
OUR HISTORY
Matthew Naylor founded Crumdale Specialty 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.”
Our Leadership
Matthew S. Naylor
EXECUTIVE CHAIRMAN
Matthew Naylor is the Executive Chairman of Crumdale Specialty and a seasoned entrepreneur and insurance executive with a proven track record across the insurance industry. Throughout his career, he has built, scaled, acquired, and led high-growth businesses, with a focus on strategic growth, operational excellence, and long-term value creation.
His expertise spans employee benefits, risk management, MGAs, MGUs, reinsurance, and mergers and acquisitions. Prior to founding Crumdale Specialty, Matthew led the growth and acquisition of multiple insurance-related businesses and later served as Chief Executive Officer and President of the Accident and Health Division of Houston International Insurance Group.
Read more…Matthew S. Naylor, Executive Chairman
Matthew Naylor is the Executive Chairman of Crumdale Specialty and a seasoned entrepreneur and insurance executive with a proven track record across the insurance industry. Throughout his career, he has built, scaled, acquired, and led high-growth businesses, with a focus on strategic growth, operational excellence, and long-term value creation.
His expertise spans employee benefits, risk management, MGAs, MGUs, reinsurance, and mergers and acquisitions. Prior to founding Crumdale Specialty, Matthew led the growth and acquisition of multiple insurance-related businesses and later served as Chief Executive Officer and President of the Accident and Health Division of Houston International Insurance Group.
Matthew has also played a significant role in the development and growth of several high-performing ventures, including Syndra Capital Partners, Leverage Health Solutions, and Health Insurance Innovations (HIIQ). His accomplishments have earned notable recognition, including Ernst & Young LLP’s Entrepreneur Of The Year® Award in 2020, inclusion in the Philadelphia Business Journal’s 40 Under 40 and the AIM Institute for Learning and Research Leadership award in 2025.
In addition to his professional achievements, Matthew is the Founder of the Crumdale Family Office and has served on numerous public, private, and nonprofit boards. He currently serves as Chair Emeritus of AIM Academy and formerly served on Drexel University’s Board of Trustees. His leadership is distinguished entrepreneurial vision, and a longstanding commitment to creating meaningful and enduring impact.
Mandy DiIenno
CHIEF OF STAFF TO EXECUTIVE CHAIRMAN
Mandy is Chief of Staff to Crumdale’s Executive Chairman. Mandy is responsible for supporting the execution of Matt Naylor’s strategic vision and overseeing critical projects that drive the company’s success. In her role, she manages the progress of key initiatives, delivering detailed management reports to ensure alignment with company goals, and coordinates cross-functional teams to drive results.
Read more…Mandy DiIenno, Chief of Staff to Executive Chairman
Mandy is Chief of Staff to Crumdale’s Executive Chairman. Mandy is responsible for supporting the execution of Matt Naylor’s strategic vision and overseeing critical projects that drive the company’s success. In her role, she manages the progress of key initiatives, delivering detailed management reports to ensure alignment with company goals, and coordinates cross-functional teams to drive results.
Mandy joined Crumdale in February 2024, bringing with her a diverse background in financial management, operations, and strategic planning. She is currently overseeing all phases of Crumdale’s new headquarters development, from planning and design to construction, ensuring the project is executed on time and within budget.
Prior to her current role, Mandy was the Controller at a chemical manufacturing company, where she led financial reporting, system implementations, and process optimization across multiple entities. She also played a critical role in cash management and financial due diligence, preparing the company for potential transactions. Before that, Mandy served as the Director at a private duty home care company, where she contributed to scaling the business from a startup to a multi-million-dollar enterprise, supporting M&A efforts and due diligence leading to the successful sale of the company.
Mandy holds an MBA and a BS in Communication from the University of Miami, with a dual major in Broadcast Journalism and Political Science. Her previous startup experience enhances her ability to thrive in dynamic environments like Crumdale.
Bridget Keeley
CHIEF MARKETING & PEOPLE OFFICER
Bridget leads Crumdale’s integrated marketing, communications, culture, and learning & development strategies, aligning brand and people to drive growth, engagement, and long-term impact. In her role within the Office of the CEO, she is responsible for shaping both the external market narrative and the internal employee experience—ensuring they are deeply connected and mutually reinforcing.
Read more…Bridget Keeley, Chief Marketing & People Officer
Bridget leads Crumdale’s integrated marketing, communications, culture, and learning & development strategies, aligning brand and people to drive growth, engagement, and long-term impact. In her role within the Office of the CEO, she is responsible for shaping both the external market narrative and the internal employee experience—ensuring they are deeply connected and mutually reinforcing.
With over 25 years of global experience, Bridget specializes in humanizing brands and building high-performing, purpose-driven organizations. Her expertise spans strategic marketing, storytelling, brand development, employee engagement, and leadership alinment—helping organizations create meaningful connections with both their people and their markets while delivering differentiated positioning and sustained growth.
Bridget joined Crumdale in 2024. She previously served as an executive at a leading wealth management technology and investment services firm, where she led global marketing and communications for the private banking business and designed enterprise client and employee experience programs. Throughout her career, she has partnered closely with executive leadership on transformational initiatives spanning strategy, culture, and growth, including helping launch a global startup within an established organization.
She holds a B.S. in Human Development and Family Studies from The Pennsylvania State University. Bridget serves on the Board of Trustees for Gwynedd Mercy Academy Elementary School and chairs its Marketing and Admissions Committee.
Jake Willcox
President, Stop Loss & Enterprise Revenue
Jake leads Crumdale’s global sales strategy. His deep industry experience and leadership in employee benefits and risk management helps ensure the success of Crumdale’s ecosystem.
Read more…Jake Willcox, President, Stop Loss & Enterprise Revenue
Jake leads Crumdale’s global sales 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. Jake continues to support the university on various fronts.
Brian J. McTear
PRESIDENT
Brian oversees the execution of Crumdale’s strategic growth initiatives.
Read more…Brian J. McTear, President
Brian oversees the execution of Crumdale’s 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.
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.
Read more…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. 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
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 Paychex, Paylocity, and Workday.
Read more…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 Paychex, Paylocity, and Workday.
Jim leads the execution of Crumdale’s Sales 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.
“We really liked the flexibility in working with the Crumdale Specialty team to make the transition smooth for our groups. Ivana is the best in the business. We love working with her. She makes our lives very easy once a deal gets through the door.”
Our Mission
To revolutionize the self-funded insurance space through innovative products and cost saving solutions that deliver better employee benefits at a lower cost.
Our Vision
At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. We are thoughtful, patient, and intentional in fostering long-term, value-based relationships with our broker and trading partners. Working together, we create cost saving solutions, better outcomes, and a better experience for employees accessing their benefits.
Our Values
Our company culture is rooted in alignment, innovation, and integrity. We believe when our clients win, we win. We become part of your team, so you can do what you do best.
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.
Let’s work together
INSURANCE ISN’T NEW, BUT THE WAY WE TAILOR IT TO MEET YOUR NEEDS IS. CONTACT US TODAY FOR A COMPLIMENTARY, CONFIDENTIAL CLIENT ASSESSMENT.
