Southeast-based agency successfully
grows with its regional operating and distributed equity models
By Christopher W. Cook
Photography by Tim Meyers
Around thirty years ago, there was an alliance of independent agencies known as Georgia Agency Partners (GAP). “It was a tightly knit group of business partners and friends who worked together. We didn’t compete and we shared ideas,” says Trae Vaughn, who was a partner of Brock Insurance Agency, a member of GAP.
Seven years ago, national and regional brokers began acquiring some of the GAP partners, who had simply run out of perpetuation options, and this led to the creation of Oakbridge Insurance. A regional firm in the Southeastern United States, Oakbridge started on January 1, 2021, with four Georgia-based agencies and a combined revenue of around $30 million.
One of its founders and now executive chairman, Robbie Smith, was a partner with Reagan Consulting earlier in his career and was one of the original authors of its Best Practices Study. “I take that study very seriously,” he says. “In the early stages of Oakbridge, two of the top five top-performing agencies in the country based on the Best Practices results partnered with Oakbridge. Those two agencies and the four original ones created the nucleus of Oakbridge and really set the foundation of excellence.” (One of those two agencies was Trae’s Chattanooga-based Brock Insurance; Trae now serves as president of Oakbridge.)
And how did the Oakbridge name come into play?
“One of our founding partners had [a logo with] a silhouette of an oak tree. It’s quite a beautiful tree. Oak trees become a permanent part of the landscape,” Robbie says.
While the word “oak” was jotted down to be included, a conversation between Robbie and his brother finalized the name. Robbie explained to him that his new company was “trying to partner with agencies that have lots of gas left in the tank, but [the owners have] taken the business on their own as far as they can; and to take the business to the next level, they’ll need investment capital, access to specialty programs, and help with carrier relationships, technology and hiring new producers.
“He said, ‘So you guys are going to be the bridge that helps them get from where they’re at to where they want to get by bringing tools, resources, and capabilities to the table.’ And I said, ‘That’s exactly right. We are the bridge.’ Hence, Oakbridge.”


Strategic growth
Today, Oakbridge has more than $200 million in revenue and 700-plus employees spread out among more than 40 locations across nine states in the Southeast. Its book of business is 60% commercial lines, 20% personal lines and 20% employee benefits.
“We’ve had strong double-digit organic growth over the last five years since inception,” says Matt James, agency co-founder and chief executive officer. “Yes, we do acquire or partner with other agencies, but we think about that as a buy-in model for those folks to access our resources and really think about driving organic growth within their local footprint.”
Robbie adds that the agency focuses strategically on like-minded agencies located in regions of the Southeast it’s interested in or ones that have specialty programs and niches that Oakbridge wants to represent. Some of the agency’s areas of specialization include construction and homebuilders, hospitality, habitational, coastal properties, surety, wood and timber products, trucking and transportation, and agri-business including crop and poultry—with agriculture being the number one industry in each state the agency has a presence.
As for its employee benefits products, “We have a book of individual health business all the way through employer groups with many thousand employees around different classes of business from financial services and technology,” Robbie says. “We have a very robust offering, [including] enrollment, compliance, communications, benefits administration, pharmacy management, HR consulting—the things that are taking work and expense off the employer.”
A key to the agency’s growth strategy is providing its new partners with resources to help their agencies develop.


“The premise of Oakbridge is to combine what we believe to be the strengths of the local agency—relationships in the community—with the resources of the larger brokers; those resources being claims, safety, loss control, technology, carrier relationships, and to create a better outcome for our clients and through the client’s full cycle of their business,” Robbie says. “We always want to lean towards the relationship side of the equation, but what we recognized is that to best serve our clients required a level of resources and sophistication that most local agencies didn’t have.”
To aid with this, a business plan of standard operations, known as One Oakbridge, was created for every partner agency, which sees every location using the same agency management system and following a standard approach from producer, staff and account manager compensation plans to back-end office functions and training and development.

“We adopted a producer training program that was developed by Randy Schwantz [with The Wedge Group],” Robbie says. “We hired one of Randy’s key trainers, Cynthia Moench, so that we’re able to hire, identify and train this next generation of producer talent, and Randy continues to play a key role in our producer hiring and development process.”
Speaking of the next generation, in July, Robbie stepped down as chief executive officer, part of a strategic plan that shifted positions amongst team members. “Matt recently became the CEO; Trae became the president; and John [Ledyard] has been the chief operating officer for some time,” says Robbie. “A big part of what we’re doing is staying ahead of the demographics of the business.”

Employee owned
One way the agency has stayed ahead is by offering ownership in the agency to its team members.
“We have outside capital that helps us facilitate partnerships and investment in talent and technology, but employees are the majority owners of the business, and that’s not just with former principals of agencies we partner with, but that’s distributed throughout the ranks, [including] back-office, account managers, and receptionists,” Matt says. “We think about getting ownership in the hands of as many folks as possible. As we say, ‘the table is round,’ you just have to show up to be part of the process.”
“We have multiple paths to ownership,” Trae adds. “As part of all our new partnerships, we often see a heavy amount of equity rollover during those transactions. Oftentimes, we also see that the equity goes beyond the legacy ownership group; it goes to the folks who probably should have owned equity at the time of the transaction, whether they’ve been driving a lot of new business over the last several years or they’re key senior account managers who have really helped with retention.”
The agency also has a producer-earned equity program, where producers earn equity grants against the growth of their books of business, as well as an equity nomination program that covers non-producer shareholders.
“A new program we just started in July is a cross-sell initiative among lines of business that creates an equity pool that all producers can participate in to encourage cross-selling among benefits, commercial, personal, surety, etc.,” Trae adds. “We are constantly looking for avenues to allow the people who really drive the business to have a real equity stake. It’s key for us to drive down our average shareholder age and continue to perpetuate the ownership of the business for the long term.”

Regional approach
Early on, Oakbridge made the choice to remain a regional agency, focusing on the states in the Southeast. “We feel like we can get to scale much more quickly by staying regional as opposed to going national,” Robbie says. “We’re in a lot of college towns. We love them because there’s just energy and a vibrancy around what goes on.”
“You’re not going to see Oakbridge’s name on a major league baseball stadium, but you’re going to see our name at the local high school baseball field and on the jerseys of the little league teams in our communities where we’re coaching and our children are playing,” Trae adds.
With a footprint spread across several offices in multiple states, the agency is divided into five regions run by regional managing directors (RMDs). “They tend to be senior shareholders or top producers who previously ran their legacy businesses [prior to joining Oakbridge], and are supported by directors of operations (RDOs),” Trae says. “The RMDs are in the field, running the day-to-day and making decisions while the RDOs are supporting by driving home a customer-first mentality with our customer service colleagues.”
These decisions include community involvement like charities supported, boards served on, and participation in local events.
“I’m based in Chattanooga and one of my business partners and I have both been very involved with the Boys & Girls Clubs of Chattanooga,” Trae says. “We’ve served on the boards, participate in their events, and contribute to their annual fundraising. Down in our Atlanta market, one of our regional managing directors, Mike Iverson, has been very involved with the Bashor Men’s Homeless Shelter. He helped procure a high-impact grant through one of our insurance carriers this past year. These are just two examples of many community-based investments we encourage as a business.”
While regional staff appreciation events occur for account managers and customer service staff, Oakbridge does bring team members across all regions together throughout the year for various events.
“We have a trip each year for our Chairman’s Club, which is made up of the top producers in the company,” Trae says. “We curate these events and they turn into relationship building amongst our production staff. All of this is done to drive a culture of One Oakbridge.”
“We don’t leave out the back-office folks,” adds Matt. “In July every year we have our accounting summit. Our other functional areas like IT and HR typically have a summit, as well. With the number of locations we have, our folks are spread out, so we’re very intentional about getting [teams] together at least once a year, and oftentimes more than once a year, to build that rapport and get them to see folks in person.”
“Our culture is built by consistency and adhering to our core values and has little to do with proximity,” says John Ledyard, chief operating officer. “We look at the in-person time together as a compounding factor to drive our core values and our culture forward.”
Tech forward
Looking forward to the future of insurance operations, the agency continues to focus on the strategic adoption of technology for customer service and other tasks. “We believe in choosing the right technology for the customer, not just to chase technology for technology’s sake,” John says. “Every investment in technology has to answer one question: Does it help us make our clients better?”
The agency uses Applied Epic as its core agency management system, Bignition (which is a product of Randy Schwantz’s) as its primary customer relationship management (CRM) platform, Microsoft Dynamics 365 Business Central as its enterprise resource planning platform for its back-end tasks, and a variety of other CRMs for its various benefits practices.

Investing in the agency’s general data platform has also been a priority. “There were reports that we couldn’t reproduce [from our systems], so we took a proactive approach building out a robust reporting suite using Databricks and [Microsoft] Power BI as our visualization tool,” John says. “We’ve taken a very back-end approach to generate the reports that we need to run the business and make sure that we’re performing within that top quartile or decile but not doing so at the sacrifice of our clients or our account management staff. Our data analytics platform is critical to what we’ve been doing over the last 18 months.”
Customer self-service tools are available for some tasks as well. “[Applied’s] CSR24 is something that we are currently utilizing, especially for our certificate delivery, but also in our small commercial and personal lines space,” John says. “There are so many tools and technologies out there. Some of them are made for our convenience but positioned as the clients’ convenience, [but our clients still] need to know who their agent is and how to get in touch with them. CSR24 is a great tool for that.
“We’re also now venturing into real enhancements from an AI perspective,” John adds. “We’ve been implementing LangSmith, which is our orchestration platform for all our agentic AI development that we’re doing, inclusive of building a couple of proprietary products in-house, largely on the support side.”
With its smart usage of technology, organic-growth mentality, and regional operating and distributed equity models, Rough Notes is proud to recognize Oakbridge Insurance as our Agency of the Month.





