Existing Executive Leaders Step into Expanded Roles in Planned Transition; Robbie Smith to Become Executive Chairman; Matt James Named Chief Executive Officer; Trae Vaughan Appointed President

Oakbridge Insurance, one of the largest privately owned insurance brokerages specializing in commercial P&C, employee benefits, surety, personal insurance, and life & health services, today announced a planned leadership transition designed to support the company’s continued growth and long-term strategic vision.

Effective July 1, 2026, Robbie Smith, President and Chief Executive Officer, will transition to the role of Executive Chairman. Matt James, currently Chief Financial Officer and Chief Acquisition Officer, will step into the role of Chief Executive Officer, and Trae Vaughan will assume the role of President after serving as Managing Director. These leadership appointments reflect the continued evolution of Oakbridge’s executive leadership team, while maintaining Oakbridge’s employee-centric operating model as the company continues to grow organically and through acquisitions.

“Over the past several years, we have built a firm defined by trusted relationships, service without compromise, and a commitment to always doing what is right for our colleagues, clients, and carrier partners,” said Robbie Smith. “I am incredibly proud of what our team has accomplished so far and confident that Matt, Trae, and our broader leadership group will build on our current momentum as Oakbridge enters this next phase of growth.”

As Executive Chairman, Smith will continue to guide the company’s strategic direction, develop talent, and cultivate new partnerships.

“The vision and mission of Oakbridge remain unchanged,” said James. “We are doubling down on what has made us successful: a broadly aligned employee-centric model that empowers both the current and next generation of talent. Together with Robbie, Trae, and our executive team, we are well positioned to scale strategically while continuing to invest in our people and expand our capabilities.”

James brings deep financial, operational, and acquisition expertise to his new role. As EVP, Chief Financial Officer, and Chief Acquisition Officer at Oakbridge, he has led the firm’s financial, legal, and M&A functions since inception, driving inorganic growth, strategy, and disciplined capital allocation.

Prior to Oakbridge, he served on the executive team of a private equity-backed insurance distribution business where he oversaw corporate finance and enterprise-wide growth initiatives. His experience building scalable organizations and driving disciplined execution equips him to lead the company’s next chapter focused on sustainable value creation and intentional, strategic expansion.

As Managing Director of Oakbridge’s largest region, Vaughan serves as both a producer and leader within the firm’s sales-focused organization. Having progressed in his career through the agency business, he developed an early appreciation for the independent brokerage channel and the opportunities it creates for entrepreneurial producers. Vaughan brings the perspective and energy of a top producer and will focus on strengthening and expanding Oakbridge’s producer-centric culture.

“This transition strengthens our ability to serve producers and clients at every level, creating the ideal environment for sustainable organic growth,” said Vaughan. “Our focus remains squarely on empowering producers through income, equity opportunities, and resources, developing future leaders to deliver results that matter. In the role of President, I look forward to working with our producers and clients, providing the superior level of support and service Oakbridge is known for within the industry.”

Together, these leadership appointments mark an important milestone in Oakbridge’s evolution and reaffirm the company’s commitment to delivering exceptional outcomes for clients, colleagues, and partners.

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About Oakbridge

Oakbridge Insurance is a top 50 insurance brokerage in the U.S. and a leading regional insurance and risk management firm with deep specialty and niche market expertise. Backed by a people-first culture and powered by the “One Oakbridge” operating model, Oakbridge delivers customized P&C, benefits, and specialty solutions across industries. Learn more at oakbridgeinsurance.com.

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Together, these leadership appointments mark an important milestone in Oakbridge’s evolution and reaffirm the company’s commitment to delivering exceptional outcomes for clients, colleagues, and partners.