Executive Team
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Charles Caldwell
Chief Executive OfficerMr. Caldwell has over fifty years of experience in the insurance industry, the majority of which have been in management positions of managing general agencies. ...
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Richard Bird
Chief Operating OfficerMr. Bird joined Midlands in October 2007 and serves the Company as Chief Operating Officer.
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Colin Caldwell
Executive Vice PresidentMr. Caldwell serves as the Executive Vice President for Midlands. He has been very active in Midlands’ boat program and is responsible for underwriting and...
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Dennis Ottis
Mr. Ottis joined Midlands in 1995. He leads all accounting related duties including financial reporting, implementation of internal controls, and tax returns...
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Sheryl Case
Senior Vice PresidentMs. Case has over twenty years of experience in the Insurance industry and has been with Midlands since 1994, working in various underwriting positions. She...
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