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.  He currently serves Midlands as Chief Executive Officer.

Mr. Caldwell founded Midlands in 1990 and was responsible for planning and developing Midlands from the start-up phase and continues to be the driving force in the development of new programs and in the tremendous growth Midlands has experienced.  He is also experienced in captive formation and reinsurance negotiation.  Mr. Caldwell is active in the management of a large book of primary and excess workers’ compensation business.  He is recognized as an authority in self-insured workers’ compensation and insurance pools, and has participated as a speaker in numerous insurance seminars.

In addition, Mr. Caldwell has managed numerous property and casualty programs over the span of his career on an MGA wholesale basis.  The management of these programs include production, underwriting and claims supervision.  The underwriting programs span to the private and public sector as well.

Mr. Caldwell has received various industry awards in recognition of his efforts on behalf of the property and casualty insurance industry by his involvement in trade associations, professional societies and the promotion of educational and civic duties. Mr. Caldwell is a longstanding Coverholder at Lloyd’s of London and former member of Lloyd’s.