Articles from Oakbridge Insurance
Oakbridge Insurance, one of the largest privately owned insurance brokerages in the United States, announced that the executive leadership transition is now complete. Effective today, Robbie Smith assumes the role of Executive Chairman, Matt James becomes Chief Executive Officer, and Trae Vaughan takes on the position of President, joining existing COO John Ledyard to complete the firm's senior leadership team.
By Oakbridge Insurance · Via Business Wire · July 1, 2026
Oakbridge Insurance Agency LLC, a U.S. Top 50 independent insurance brokerage, is pleased to announce a partnership with Earl Bacon Agency, a Tallahassee‑based insurance firm with more than 60 years of experience advising families, businesses, and nonprofit organizations across Florida’s Panhandle.
By Oakbridge Insurance · Via Business Wire · May 27, 2026
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.
By Oakbridge Insurance · Via Business Wire · March 23, 2026

Oakbridge Insurance, one of the Southeast’s largest privately owned insurance agencies announces the appointment of John Ledyard as Executive Vice President and Chief Operating Officer. Ledyard brings to Oakbridge a proven record of delivering exceptional results. He effectively combines agency expertise with a passion for operational excellence, bringing energy and innovation to Oakbridge.
By Oakbridge Insurance · Via Business Wire · March 10, 2025