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.
Jimmy, Jimmy, Jimmy, Jimmy. Welcome to the show.
Jim Andrews: Excited to be here.
Matthew Naylor: It’s going to be a fun one.
Jim Andrews: Oh, yeah. I’m ready to go. Let’s let it rip.
Matthew Naylor: I love starting these conversations with the audience getting to know you a little bit—your lived experience, where you’re from, how you were raised, and where you went to school. This podcast is about alignment and impact, sitting at the intersection of healthcare and entrepreneurship. Your background and your role with Crumdale Specialty speak volumes to that, and I’d love for you to start with your story.
Jim Andrews: Sure. I guess we could start way back. I grew up originally in East Falls, which is a tough little neighborhood in North Philly. Philadelphia is a very parochial town; we go by parishes, so you understand the neighborhood you’re from. My dad was a Philly policeman and my mom stayed at home with me and my two younger brothers. Eventually, we moved to Northeast Philadelphia, which was an up-and-coming region where a lot of police and firemen went for a little more land and a less urban feel.
My dad was an undercover policeman, but he was also my first coach and mentor. East Falls people are humble, simple, and tough—at the old stadium, they’d be up in the 700 level in the elements, not in the boxes. It was a hardscrabble, middle-class neighborhood where loyalty was everything.
Matthew Naylor: When you think of East Falls, what’s the go-to food? What’s the best pizza?
Jim Andrews: I was actually more of a cheesesteak guy than a pizza guy. Dalessandro’s in Roxborough was, and always will be, my number one. I also used to go to Mama’s in Bala Cynwyd and Chubby’s. To me, the cheesesteak identifies East Falls more than the pizza does.
Matthew Naylor: Did you grow up playing sports?
Jim Andrews: Yeah, a ton of them. My dad was a great athlete—football, baseball, basketball, tennis—and I wanted to be just like him. I actually played a lot of soccer and baseball growing up. I played for the Ukrainian Nationals, which was my entree into soccer at seven or eight years old. I eventually moved into becoming a goalkeeper for most of my career.
Matthew Naylor: I love the goalie thing because it speaks to your leadership approach. Where did you go to college?
Jim Andrews: I went to several schools. College wasn’t what I wanted it to be because I kept hurting my knee and transferring to get myself rehabbed. I was the first one in my family to go to college, but at the time, I was immature and education wasn’t as important to me as playing sports. It wasn’t until I got a little older and saw what success looked like at Chestnut Hill Academy that I started realizing what I could be. Later, I coached Division 1 soccer at Philly Textile for five years. That was a great experience because Textile was a powerhouse with a big international presence. I learned a lot about loyalty and treating people the right way by seeing teammates from different backgrounds become best friends.
Matthew Naylor: How did you make the transition from a soccer coach to your professional business career?
Jim Andrews: I thought I was going to coach forever, but I wasn’t making any money. I realized I had to “grow up” and get a real job. I worked at SEPTA, was a gym teacher, bartended, and eventually finished my degree at Cabrini. My first real business entree was with Philadelphia Trolley Works in a hospitality role that combined ops and sales. I realized I was a natural salesman and recruiter.
Eventually, I got a job at Paychex. I was surrounded by a great team—one of the best in the country—and I started seeing success. People began valuing my opinions and my work ethic. But I’m never satisfied; I always want the next challenge. I later took a job at Workday, which was an incredible company, but I worked for someone I didn’t trust, so I exited. I actually quit without another job lined up, which was the first time I’d ever done that. I called Mike Caskey at Paylocity, and he offered me a role at half my previous salary to open a new market. I was Rookie of the Year, broke every record, and moved into leadership. I spent 10 years there, watching the company grow from under $60 million in revenue to a $16 billion market cap.
Matthew Naylor: So how did you learn about Crumdale Specialty?
Jim Andrews: Crumdale was waiting for me. A recruiter friend, Brad Lyons, sent me a job listing and said it was something I should look at. I read it and thought, “This is me”. I went through a long interview process—about six months. The final interview was a dinner at your farm with the partners and our wives. We were there for five or six hours having an unbelievable time. On the walk to the car, my wife said, “I get it. I’m in”. She knew these were the people I believed in and it was the right fit.
Matthew Naylor: At that point, you weren’t an expert in healthcare or PBM services; you were an expert in leadership and sales organizations.
Jim Andrews: Right. I understood people. You told me that teaching me insurance was the easy part; the hard part was taking my skills and implementing them into a healthcare system that is broken and doesn’t want change. You never said “no” to my ideas. I spent about six months just building out the business plan, writing on whiteboards for hours like a mad scientist.
Matthew Naylor: You started at Crumdale Specialty when we had no sales organization. Tell us about that journey.
Jim Andrews: It’s been a fun ride. We wanted to find people who were willing to do things differently and hold a standard that wasn’t being met in this space. You guys trusted me to put together a plan and let me be myself. I started at the basics: recruiting standards, building a marketing brand, and training. I’m a big believer in the Challenger Sale and Nick Saban’s idea that “the standard is the standard”. Today, the team has grown from a few people to about 60, and we’ve been recognized as an Inc. Magazine Best Place to Work.
Matthew Naylor: When did you first realize the culture here was something special?
Jim Andrews: It was a Sunday when a client was ripping into us. I called Jake, and your response was that Sunday is for family and anything can be fixed on Monday. Monday morning, you came in and said we aren’t going to work with people who don’t treat others with dignity and compassion. We fired that client immediately. That was the buy-in moment for me—realizing you actually lived the “family first” mantra rather than just saying it.
Matthew Naylor: What is something about our team that outsiders may not realize?
Jim Andrews: We aren’t just a “family”—we’re a community. We know each other’s families, we’ve been in each other’s homes, and those relationships are real. We’re a family-oriented organization competing against massive giants, and everyone here runs at a high rate.
Matthew Naylor: How do you spot a Crumdale person when you meet them?
Jim Andrews: It’s DNA. They work hard, they believe in the company ethos, and they hold a standard of excellence. They are like elite athletes—humble, focused on “we” instead of “me”.
Matthew Naylor: Any funny Crumdale stories that haven’t been told publicly?
Jim Andrews: The intern program was a classic. For their final project, I gave them two options: they could get a “businessy” haircut (a tonsure/old person cut) or present in 1776 garb with a British accent. One of the kids actually chose the haircut and showed up at my house at 11:00 PM looking 42 years old. His mom wasn’t happy, but he’s in our Hall of Fame now. The other kids showed up in the English garb and did their whole presentation in British accents. We didn’t have HR back then!
Matthew Naylor: Let’s close with a lightning round. First big win at Crumdale?
Jim Andrews: Getting the approval to hire our first person, Scott Brenmore.
Matthew Naylor: Craziest meeting?
Jim Andrews: Meeting Lou Alamo in Newark. We ate enough food to feed a whole village at noon, and they weren’t even drinking—it was just an unbelievable experience.
Matthew Naylor: One word to describe Crumdale?
Jim Andrews: Community.
Matthew Naylor: Best advice you’d give your younger self?
Jim Andrews: It’s the journey, not the result. Focus on the journey because that’s where everything actually happens.
Matthew Naylor: Most underrated quality Crumdale possesses?
Jim Andrews: 100% grit. We may look fancy or classic, but we will go toe-to-toe with you all day. Don’t pick a fight with us.
Matthew Naylor: Jimmy, thanks for being part of the show today. Awesome.
Jim Andrews: Thank you.
Matthew Naylor: This is Matthew Naylor. You’ve been listening to Aligned for Impact.
