June 28, 2022

For Brandon Pittman and Hasten McDermott, their relationship in the insurance business started as a competition, one that would ultimately lead them to where the Pittman Insurance Group is today, Oakbridge Insurance’s partner agency.

As a producer in Raleigh, Hasten McDermott often met his annual sales quota in August or September. “I always thought I was done for the year, top dog, but there was this other guy in my region who would always appear out of nowhere and give me a run for my money.”

That other agent was Pittman. “I’m a networker and socializer. Hasten is the numbers man, methodically plodding his way along, efficient and smooth, then I would come along in the fourth quarter and beat him.”

Competition between the two ambitious young producers grew to a mutual respect of each other’s work and a growing curiosity about the other’s success. In 2015, Pittman bought the agency where he worked and quickly hired McDermott. Thus, the Pittman Insurance Group was formed.

Together, they knew they could do more.

The Pittman Group continued to build its business, establishing a niche market in construction and later expanded its multi-family lines and made new headway writing policies for owners of high value homes. “I promised Hasten I would show him how to do $150,000 in revenue a year,” Pittman says.

McDermott worked alongside Pittman to lead the firm’s growth and became partner in 2019.

“It’s been a great relationship,” Pittman says. “We have very different skillsets, he’s analytical and I thrive on personal interaction. We’ve played off each other’s strengths to evolve and build this business to where it is today. I’m glad we don’t have to compete. I would have to work a lot harder today to beat Hasten,” he says with a laugh.

One challenge for Pittman and McDermott has been remaining relevant, both in terms of meeting market demands and providing an increased level of service for clients. Recruiting and training producers has also been a challenge in a tightening jobs marketplace.

“We began to look at the business and think about the next decade,” McDermott says. “Part of that process was a business valuation exercise. It really opened our eyes to both the value of what we’d built and also to the firm’s potential for expansion.”

They approached a broker to begin assessing potential partners. “On paper, we figured there were maybe four companies we’d feel comfortable combining forces with,” Pittman explains. “Once we started talking, there really was only one – Oakbridge.”

Pittman adds, “it came down to culture and capabilities. Hasten and I balance each other so well…the numbers guy and the people person. We needed to scale with the same kind of partner. Oakbridge’s personality mirrored ours:  a culture of commitment to its people – clients and associates – and an operating philosophy that’s best in the business.”

Pittman and McDermott are excited about the future. “We bring a great footprint in the Carolinas to Oakbridge. Our multi-family expertise adds to the Oakbridge portfolio, and our proactive services work meshes well with theirs,” McDermott notes. “We’ll have the operational and technological support to free us up to focus on really growing our business.”

“We’re like family,” Pittman says of their employees, “and Oakbridge approaches it the same way. They’re people-centric but also very sophisticated in how they do business and how they approach expansion. We’ll be able to return to focusing on organic growth and that’s very important for both of us.”

“I’m thrilled to be able to return to producing and taking care of clients! We’ve now got the resources to really take this business to the next great phase of its journey. It’s a very exciting time!”

Indeed. Oakbridge continues to grow stronger through alliances and partnerships with agencies like Pittman. We’ve been working together to protect our neighbors and communities we serve for nearly 100 years. We’re Oakbridge – deeply rooted in relationships.

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