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Who We Are

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Carole Fleischman is the Cheif Executive Officer of Pioneer Programs Insurance Solutions, LLC where she oversees the development, underwriting and administration of the national programs. Prior to joining Pioneer in November, 2008. Carole was President of the Managed Insurance Programs division since 1998. Previously Carole was the Senior Vice President at Stewart Smith West where she created their Nationwide Programs Department and handled the negotiations of a Contracting Program, as well as a Courier and Nursing Home Program. Before that, she was the Managing Vice President and Senior Vice President at Alexander Howden North America. She also spent time as an Underwriter and Branch Manager at Industrial Underwriters. Her career started out at CNA Insurance before moving on to General Accident Group and Hartford Insurance Company.

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Our Firm


Pioneer Programs Insurance Solutions, LLC (Pioneer) was formed in November of 2008 for the purpose of writing specific insurance programs on behalf of selected carriers. Although the company was established in 2008 the main stay program, Contractors’ Choice, was created in 1996 by Ms. Carole Fleischman, to insure Projects and Wrap-Ups. Like any program that is established by Pioneer, Contractors’ Choice is loss control driven. The loss control elements contain sophisticated risk management tools along with forensic risk management. By adding risk selection and pricing these elements have assured the continued success of the program in excess of 15 years.


Pioneer is focused on underwriting exceptional risks while assisting the insureds in managing their exposures. Pioneer continues to look for opportunities on to develop new niche programs that can add value to its carrier partners and insureds.

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