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Diane Westbrook has a diverse work experience spanning several industries. Diane began their career at Majestic Mortgage in 2002 as the Executive Vice President of Operations, where they worked until 2006. Following this, they joined Cherry Creek Mortgage as a Mortgage Underwriter, a role they held for twelve years until 2018. Currently, Diane is employed at BrightStar Care, where they started in 2019 as an Operations Support Coach before being promoted to Director of Operations and Training in May 2023.

Diane Westbrook completed their high school education at Libertyville High School from 1987 to 1991. Diane then pursued a Bachelor of Science degree in Child Development from Northern Illinois University, where they studied from 1991 to 1995.