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In this episode of Tell Us Your Story… Welcome to the Arena, we sat down with someone who’s walked the winding road of the insurance industry and lived to tell the tale — Kevin Carlin, Regional Sales Manager at Claremont Insurance Services. What started as a conversation about career paths turned into something much deeper: a lesson in humility, perseverance, and the power of human connection.
From Basketball Dreams to Career Detours
Kevin’s story starts in Pasadena, California — one of four boys in a tight-knit, middle-class family. Competitive by nature, Kevin grew up with a love for sports, especially basketball. But like so many of us, his dreams ran headfirst into reality when he was cut from his high school team. That moment, though painful, became a turning point.
“I wish I had a redemption story where I came back the next year and made varsity,” Kevin told us, “but it didn’t happen that way.” What did happen, though, was a journey of growth, through college and beyond, marked by grit and resilience.
Arena Lesson: Life Doesn’t Always Go According to Plan — and That’s Okay
Kevin didn’t enter college with a clear goal. In fact, he barely applied. But thanks to his mom’s encouragement (and a surprise campus tour involving a stunning campus and a charming guide), he enrolled at the University of San Diego, where he studied international relations — a far cry from the insurance industry he would one day thrive in.
His early career was filled with twists: one role after another, a series of mergers, acquisitions, and pivots. Lincoln → Take Care → FHP → MetLife → United → Seabury & Smith… the list goes on. While some might look at his résumé and see instability, Kevin reframed it for us: “I grabbed a person or two or three from every place I’ve ever been and stayed in touch with them.”
It’s not just about the job — it’s about the people.
The Humana Chapter: When Hard Work Meets the Right Moment
After experiencing layoffs, Kevin found himself unemployed for eight months — humbling and disorienting. But then came a spark: an interview with Humana. Suit purchased by his brother, pep talk in the parking lot, nerves at full tilt. He got the job. And then he got to work.
He didn’t just show up. He stayed late. Mailed physical packets. Customized proposals with client logos. Picked up the phone when others wouldn’t. “It was a magical time in my career,” Kevin recalled. “That first big win led to others — and soon, I was on a run I’ll never forget.”
Arena Insight: When You’re in the Arena, Go All In
That story — of betting on yourself, putting in the work no one sees, and turning momentum into mastery — is why we started this podcast.
We’ve always believed in giving value first. Kevin’s LinkedIn journey mirrors that belief. After missteps and a few overly eager pitches, he found his rhythm: “Give first. Help first. Then maybe, later, ask.” Now he uses the platform to spotlight HR professionals, job seekers, and industry peers — building bridges and creating opportunities for others.
Claremont, Community, and the Power of Partnership
Today, Kevin brings his experience to Claremont Insurance Services, a boutique general agency built on relationships and service. As Kevin put it, “We always want the broker to be the hero of the story.”
At Arena, we get it. That’s exactly how we see our partners, too.
GAs like Claremont are more than quoting engines — they’re an extension of your team. The ones double-checking underwriting, supporting enrollments, building out Ease, and catching the details that could derail a case. When you’re building something special, the people standing next to you matter.
Final Word from the Arena
If Kevin’s story teaches us anything, it’s this: The path doesn’t have to be perfect. You just have to keep walking it. Through career changes, personal loss, and unexpected pivots, Kevin showed up — for himself, for others, and now for his brokers.
We’re proud to work alongside people like him.
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