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Cindy Gilmore has extensive work experience in the real estate industry. Cindy started their career in 1990 as a Sales Representative at Heritage Fine Homes. Cindy then worked at Town and Country Homes as a Sales Manager from 1987 to 1996. In 1996, they joined Hearthstone as a Vice President and Senior Investment Manager, responsible for managing a portfolio and overseeing projects in the Midwest region. Cindy later became the Senior Vice President at Hearthstone, leading new business origination and development.

Cindy Gilmore's education history includes attending the University of Oklahoma. However, no information is provided regarding the specific degree or field of study nor the start and end years of their time at the university.