Executive Team

  • Charles Caldwell

    Chief Executive Officer

    Mr. 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 Officer

    Mr. Bird joined Midlands in October 2007 and serves the Company as Chief Operating Officer.

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  • Colin Caldwell

    Executive Vice President

    Mr. 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 President

    Ms. 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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