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
FOUNDER & CEO
Matthew is a dynamic entrepreneur, founder, and CEO of Crumdale Specialty, where he combines unmatched industry expertise with a relentless commitment to excellence and innovation. With a proven track record across healthcare, insurance, education, environmental services, entertainment, and real estate, Matthew has built and led sustainable businesses that make a lasting impact on the people and communities they serve.
As a visionary leader, Matthew has a unique ability to identify and capitalize on growth opportunities, driving businesses to new heights while staying true to his core values of governance, collaboration, and aligning interests. His leadership at Crumdale Specialty exemplifies this approach, with a focus on providing exceptional products and services while continuously expanding the company’s capabilities.
Read more…Matthew S. Naylor, Founder & CEO
As a visionary leader, Matthew has a unique ability to identify and capitalize on growth opportunities, driving businesses to new heights while staying true to his core values of governance, collaboration, and aligning interests. His leadership at Crumdale Specialty exemplifies this approach, with a focus on providing exceptional products and services while continuously expanding the company’s capabilities.
Matthew’s entrepreneurial spirit shines through in his diverse ventures. He founded Crumdale Specialty with a focus on long-term value creation and sustainable growth. His expertise spans employee benefits, risk management, MGAs, MGUs, and reinsurance services, with a particular strength in mergers and acquisitions.
Throughout his career, Matthew has consistently demonstrated his ability to scale businesses, including his leadership at Elite, where he led the growth and acquisition of MGAs, MGUs, and employee benefits firms. After selling Elite to Houston International Insurance Group in 2015, he went on to serve as CEO and President of their Accident and Health Division, overseeing the company’s rebranding to Skyward Insurance and its subsequent public offering in 2022.
As a partner and investor in Leverage Health Solutions, Matthew has contributed to hundreds of millions in revenue growth for innovative companies in the health insurance space. His role as lead investor and architect of Health Insurance Inc. (HIIQ) further solidified his reputation for identifying, developing, and scaling successful ventures, making HIIQ the second-largest short-term medical insurance distributor in the country.
A recognized leader in his field, Matthew has been honored as the Entrepreneur of the Year by Ernst & Young LLP in 2020 and was named to the Philadelphia Business Journal’s prestigious 40 Under 40 list in 2008. His business accomplishments have earned recognition on the Inc. 5000 list of America’s Fastest-Growing Private Companies (2021-2024), as well as Inc. Magazine’s Best Workplaces (2020-2023) and Philadelphia Business Journal’s Best Places to Work (2020).
Beyond his entrepreneurial pursuits, Matthew is deeply committed to giving back. He serves on several public, private, and nonprofit boards, including as Chair Emeritus for AIM Academy, one of the country’s top institutions for learning deficiencies. As a member of the Drexel University Board of Trustees and active participant in the Young Presidents’ Organization (YPO), Matthew’s leadership extends beyond business to education and community development.
As a dyslexic learner himself, Matthew faced many challenges growing up as he tried to navigate an often cruel and unfair world. His own lived experience has genuinely shaped the man and leader he is today. He learned along the way the power of being resourceful, relentless, and resilient – these attributes show up in everything he does professionally and personally. Matthew’s journey is marked by a passion for making a meaningful impact, and his unwavering pursuit of excellence continues to inspire those around him.
Mandy DiIenno
CHIEF OF STAFF TO FOUNDER AND CEO
Mandy is Chief of Staff to Crumdale’s Founder and CEO. Within the office of the CEO, 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 Founder and CEO
Mandy is Chief of Staff to Crumdale’s Founder and CEO. Within the office of the CEO, 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 & COMMUNICATIONS OFFICER
Bridget oversees Crumdale’s marketing, communication, culture and education strategies, working within the Office of the CEO. She brings over 20 years of extensive global experience in humanizing brands and engaging with and connecting audiences. Her expertise in strategic marketing and communications, brand management, emotional storytelling and stakeholder community development helps amplify the unique Crumdale story and culture, while delivering differentiated market positioning.
Read more…Bridget Keeley, Chief Marketing & Communications Officer
Bridget oversees Crumdale’s marketing, communication, culture and education strategies, working within the Office of the CEO. She brings over 20 years of extensive global experience in humanizing brands and engaging with and connecting audiences. Her expertise in strategic marketing and communications, brand management, emotional storytelling and stakeholder community development helps amplify the unique Crumdale story and culture, while delivering differentiated market positioning.
Bridget joined Crumdale in 2024. She previously served as an executive for a top wealth management technology and investment services firm where she led marketing and communications globally for their private banking business as well as designed and directed robust client and employee experience programs. Throughout her career, she has collaborated with and advised the C-suite on a variety of marketing, communication, strategy and culture initiatives, and was part of a leadership team responsible for launching a global start-up business within an established company.
Bridget earned a B.S. in Human Development and Family Studies from the Pennsylvania State University. She currently serves as a member of the Board of Trustees for Gwynedd Mercy Academy Elementary School and is also their Marketing and Admissions Committee Chairperson.
Brian J. McTear
PRESIDENT
Brian leads Crumdale’s day-to-day operations and the execution of our strategic growth initiatives.
Read more…Brian J. McTear, President
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 Willcox
President of 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 of 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.
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.
Read more…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. 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.
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.
