Matthew Naylor: Welcome to Alignment for Impact. I’m your host, Matthew Naylor. I started this podcast because healthcare and leadership both come down to the same thing: alignment. When people, purpose, and performance connect, real impact happens. On this show, we’ll talk with entrepreneurs, brokers, and change-makers who are challenging what is broken in healthcare and in business to find new ways to make a difference for companies, communities, and the people they serve.
Crumdale sits at this awesome intersection of risk financing, employer health services, cost containment, and technology. But more importantly, it’s about life, innovation, being creative, disruptive, and living a life with passion and purpose. Jake and Brian, you guys are my founding partners here at Crumdale Specialty. Jake, let’s start with you. Could you tell us a little bit about yourself?
Jake Willcox: Thanks for having me, Matt. I grew up in the Philadelphia area and played Division 1 lacrosse in college. After college, I moved to New York City to work for my father in a very niche part of the insurance space—structured settlements and annuities helping to settle large personal injury and medical malpractice lawsuits. I did that for about seven years, which was a great way to hone my relationship-building skills.
Eventually, I hit a point where I needed to do something different and experience life outside of working with my father. His best friend introduced us back in 2012, calling you an “awesome young entrepreneur.” We spent about a year and a half getting to know each other personally and professionally before I came on board in 2014. You told me then to be patient and thoughtful about our approach, and almost 11 years later, we are in a position of wild success.
Matthew Naylor: The early days were a lot of fun. Brian, tell us a bit about how you ended up joining Crumdale and where you were before.
Brian McTear: I grew up in Paoli, right where our office is today. I was the youngest of seven kids and the first in my family to graduate from college. I went to Malvern Prep, where Jake also went, and played three sports there before eventually going to law school. I started my career as an M&A, private equity, and venture capital lawyer for a large firm in Philadelphia. I was doing well, but I wanted something more than just documenting someone else’s transactions.
In 2012, I moved into a high-growth business in the oil and gas industry. Around that same time, you and I met randomly through a mutual friend who told us we “needed to know each other.” As my time in oil and gas was ending and Crumdale was taking off, I jumped at the chance to move into something more entrepreneurial and collaborative. One of the biggest differences here is our culture; I came from a very political environment with a lot of “shucking and jiving,” and that company doesn’t even exist anymore. It’s been a great experience working with you and Jake all these years.
Matthew Naylor: In the early days, we focused heavily on leadership, alignment, and culture. I’d like to get both of your perspectives on how you’ve built Crumdale Specialty into such a unique business for a thriving team.
Brian McTear: When we started, no task was too big or too small. We took out the trash, moved the furniture, and set up the meeting rooms ourselves. That “chief cook and bottle washer” ethos remains today. It’s leadership from the front. I try to be available 24/7 as a resource and partner, not someone just barking orders. We are innovative and creative, but execution is the real key to our success. By partnering with the people on the front lines, we set the tone for the entire culture.
Jake Willcox: Culture and leadership start and stop with the people. We’ve done a phenomenal job of recruiting and retaining the best of the best. While we are currently driving AI and technology, it’s the people sitting side-by-side with us that allow us to execute our strategy.
We aim for alignment across three pillars: intellectual, emotional, and financial. Our team is intellectually stimulated because we are constantly changing and innovating. Emotionally, we are “culture first” and “family first,” which shows in our charity work and how we invest in our teammates. Financially, we ensure people can live well and feed their families. The hard part is checking in 6, 12, or 18 months down the road to adjust and meet people where they are as their lives and the economy change.
Matthew Naylor: Crumdale has received many accolades, like being on the Inc. 5000 list for seven years and being named a “Best Place to Work.” But leadership is also about accountability and honest conversations. Can you talk about your approach to coaching and challenging people?
Brian McTear: We have team members with incredible expertise, and we make sure they have the opportunity to meaningfully contribute to the problems we are solving. From an accountability perspective, we use a very intentional and detailed process, but we also focus on real-time feedback. I always tell people that if there was anything negative to say, they would have already heard it. We pivot and collaborate in real time so people can understand immediately if they’ve gotten off the rails.
Matthew Naylor: Let’s pivot to impact. How has impact shown up for our teammates?
Brian McTear: We are thoughtful about positioning people so they can be successful in ways they haven’t been in the past. We like pushing people out of their comfort zone. For example, our Chief Revenue Officer came from outside the insurance industry. We didn’t leave him to “sink or swim”; we supported him so he could take his game to the next level. We focus on “1+1=3″—recruiting talented people and empowering them to do things they’ve never had the responsibility to do before.
Jake Willcox: I think of it as “leaving it better than you found it.” Our retention is in the high 90s over the last 11 years (excluding sales, which has natural turnover). Because Crumdale sits at the intersection of the entire self-funded supply chain, a pharmacist here doesn’t just do clinical work—they understand how their decisions affect reinsurance, sales, and renewals. When people eventually move on from Crumdale, they leave with a much higher level of play.
Matthew Naylor: We took a very different operating approach to disrupting the employer health space—integrating risk financing, TPAs, PBMs, and tech. How has that entrepreneurial approach made an impact?
Jake Willcox: It started with the question “Why?” Brian and I asked a gazillion questions of the smartest people in the industry to understand why things were integrated the way they were. We spent the first few years discovering and learning. That approach of “Discover, Develop, and Deploy” is still consistent today. We still spend a third of our day discovering the marketplace and meeting new people to see how they fit into our unique model.
Brian McTear: The market was desperate for innovation, but nobody was putting it all together. Crumdale became the “convener.” We identified people doing things differently and integrated those disparate parts into a turnkey, transparent solution that lowers costs. In an industry that usually just pushes costs onto employees, we tailored our approach to the root causes of escalating costs.
Matthew Naylor: You guys often speak about the “Win-Win-Win-Win” solution. How does Crumdale find that alignment?
Brian McTear: In law and the oil business, there are usually winners and losers. But when Crumdale wins, our distribution partners win, the employer group wins, and the employees and their families win. Elevating that entire ecosystem is part of our vibe and is why we’ve been able to grow so quickly.
Matthew Naylor: Rapid-fire round! What is something about our team that outsiders might not know?
Jake Willcox: We have a “No Asshole” rule—now famously rebranded as the Crumdale Code. We live by it internally and externally. We’ve fired large accounts that comprised significant revenue because they weren’t treating our people with respect. We protect our team; if a broker is harassing a young producer on a Sunday, we tell them to put the phone down and we handle it on Monday.
Matthew Naylor: How do you spot a Crumdale person for the first time?
Jake Willcox: They probably have Crumdale gear on! But seriously, they are real, they work hard, and they believe in the ethos.
Brian McTear: I recently mentioned that I think more than 50% of Crumdale employees have a tattoo. That’s a significant percentage!
Matthew Naylor: One hire that totally changed the game for us?
Brian McTear: Bringing on our Chief Pharmacy Officer. He brought a level of expertise that professionalized that side of the business and helped it grow into what it is today.
Matthew Naylor: A time when you thought something was a disaster but turned it around?
Jake Willcox: That happens in every part of the business because we are constantly validating and inspecting data. When a hole shows up, we lean in, course-correct, and make it better.
Matthew Naylor: First big win for Crumdale?
Brian McTear: An early distribution partner in Florida who aligned with us philosophically and is still a partner today.
Jake Willcox: Managing the homegrown plan for a multi-billion dollar agency—that gave us real validation early on.
Matthew Naylor: One word to describe Crumdale?
Jake Willcox: Innovative vibe.
Matthew Naylor: Best advice to your younger self?
Jake Willcox: Don’t get too discouraged kissing so many frogs. You’ll find plenty of dead ends, but you’ll find the open doors eventually.
Matthew Naylor: Most underrated Crumdale quality?
Brian McTear: Determination. People are consistently surprised by our level of determination.
Matthew Naylor: When did you realize Crumdale was going to be a huge success?
Brian McTear: Early on, when I was working with Buzz to develop relationships in the Midwest. We were getting call after call from people who had never heard of us but were resonating deeply with our story.
Jake Willcox: I took my cues from you, Matt. When you decided to redo the office for a second time and extend the driveway with asphalt trucks coming in, I thought, “He must really believe we’re going to crush it because he’s spending all this money!”
Matthew Naylor: What excites you about the future?
Brian McTear: The possibilities are endless. We can build more products, leverage AI to make our people smarter, and move into near-adjacencies.
Jake Willcox: We’ve built a platform that is bigger than the three of us. We’ve created a hub that sits at the intersection of this industry and has the opportunity to evolve into the next big thing over the next few decades.
Matthew Naylor: Jake and Brian, this was a fun conversation. Everyone on the Crumdale team appreciates your leadership. Keep up the great work. This is Matthew Naylor. You’ve been listening to Aligned for Impact.
