Workers’ Comp Producer Spotlight: Charlie Deaver
In this month’s producer spotlight, we highlight Charlie Deaver, principal and co-founder of Greyhawk Premier Insurance Solutions. A long-time Arrowhead producer, Charlie shares his journey of leadership, grit and the growth mindset that drives his success in the insurance industry.
A leap of faith
Charlie Deaver didn’t grow up dreaming of selling insurance. In fact, his early days were spent selling portable toilets — a job that, while practical, didn’t quite feel like a lifelong calling. “I was doing okay,” he recalls, “but I got married young and I realized I had to do something different.”
With the kind of determination that comes from realizing you’re not where you want to be, Charlie took matters into his own hands. Like many of us faced with an existential crisis and no clear plan, he did what any rational person would do: he Googled his way out of it. “For whatever reason, I decided to look up the average age of insurance agents and it was like 55 or 56 at the time. I thought, ‘If I can get into this industry and do well, I’ll just outlast the other retirees’.”
That realization quickly set the wheels in motion. He earned his insurance license while recovering from a surgery — a perfect example of making the most out of a challenging situation. “I figured the worst thing that could happen was I’d spend a couple hundred bucks and realize I didn’t like insurance.” And just like that, Charlie was on his way.
Related: Spotlight on Workers’ Compensation Producer Craig Penrose
Greyhawk takes flight
After gaining years of experience at a family-run agency, where he learned the ropes and honed his skills, Charlie knew it was time for a bigger challenge. “The time I had with my previous agency and my old boss was incredible. He was a fantastic mentor,” he recalls. “But as much as I loved my boss, I needed to continue expanding my wings. That’s what created the need to give the entrepreneurial journey a go.”
In October 2021, Charlie and his business partner, Daniel Clarke, decided to take the leap and start Greyhawk Premier Insurance Solutions. They started small — with only one other commercial account manager and a commercial book of business — but with big dreams.
The dream grew quickly, and so did the company. “We started with one employee, and we just hired our 30th,” Charlie says, still somewhat surprised by the rapid growth. “The only thing we don’t offer at this point is pet insurance.”
Key to their success, Charlie emphasizes, is investing in people. “I’m taking kids straight out of college and I’m training them,” he explains. “It requires a lot of energy, but that’s also shown me a ton of growth in the business because I have eight guys who are brand new and just hustling like crazy.”
Mentoring young producers is a big part of what makes Greyhawk stand out. But Charlie’s commitment doesn’t stop there. “We also offer ownership,” he says. “If you’re a great culture fit, we’ll allow you to start purchasing ownership. I feel like if I want these people to be a part of my team and I want high performers, they should have the opportunity to be owners with me.”
Powered by perseverance
Despite his success, Charlie’s journey has not been without challenges. “Early on as a producer, there were moments when I thought, ‘Can I really do this for the rest of my life?’” he recalls. “Sometimes, I was whiffing on accounts or just not getting any traction. It was difficult to see the light at the end of tunnel.”
But if there’s one thing Charlie prides himself on, it’s grit. “I’ve always lived by the ability to have grit and just work hard,” he says. “It’s doing the same things over and over, and eventually results do come from it.”
That same determination was put to the test more recently as Greyhawk faced one of its biggest challenges. “Last year, we went through a merger, and I pushed the business so hard that we almost ran ourselves out of cash,” Charlie says with the kind of candor that only comes after surviving a crisis. “It was a huge learning experience. You can’t be all gas — sometimes, you need the brakes.”
Through it all, perseverance has been Charlie’s guiding principle. “There are no shortcuts in life,” he says. “It’s about being gritty, getting to the next phone call or appointment and just doing simple things, like just showing up the next morning.”
Related: Workers’ Compensation Producer Spotlight
The Arrowhead advantage
As Greyhawk has grown, Charlie has relied on strong partnerships, and one of the longest-standing relationships has been with Arrowhead. “You guys have been great for as long as I’ve been a producer and an owner,” Charlie says. “It’s always been easy working with you.”
The ease is what makes Arrowhead stand out to Charlie, especially when it comes to programs offered. “The programs are simple,” he explains. “Arrowhead has a niche, and they do it well.”
His introduction to Arrowhead came through the earthquake program, which was the first non-auto or home product he sold. “For 10 years, the only way I knew to sell earthquake insurance was through Arrowhead,” he says. And as Greyhawk has expanded, so has its partnership with Arrowhead. “Workers’ comp is now a big part of how we lead to break the door with new relationships.”
Beyond workers’ comp, Greyhawk counts the automotive aftermarket and umbrella programs in their lineup. Charlie appreciates the efficiency this brings to his team. “It’s easy for us to say, ‘Hey, you guys have a program for this, and it’s quick,’” he adds. “To have one place to stop and get two quotes is fantastic.”
Related: Workers’ Compensation Spotlight on Tyla Belton
Forward in focus
As Charlie looks ahead, he doesn’t just see a growing company — he sees the unique challenges that come with navigating today’s market. “The thing I feel we do best at Greyhawk is delivering bad news,” he says with refreshing honesty. “The reality is that everyone is going through difficult economic conditions, and the insurance market is challenging on top of that. The people who can show empathy, deliver difficult news well and provide context are the ones who are doing the best. That’s something we’re really good at.”
For Charlie, success isn’t just about offering the right products — it’s about transparency and helping clients understand the bigger picture. “We hear every objection, and we just try to walk people through it, to help them understand. It’s been good for us.” It’s this no-nonsense, yet compassionate approach that helps set Greyhawk apart.
That transparency and trust also extend to the way Greyhawk operates internally. “One thing that is challenging is finding good business partners,” Charlie says, reflecting on his partnership with Daniel and Justin Pizzola. “Everyone has different agendas, and that can be a recipe for disaster. But there’s this magic when you find two other people who align with you. We’re able to run quickly because those two guys are phenomenal at what they do.”
Ultimately, it’s trust and collaboration that have allowed Greyhawk to grow quickly and effectively. Charlie is the first to admit that it all comes down to one thing. “I have really good people,” he says with a smile. “Without them, the engine doesn’t go.”