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Kellie Cunningham has a work experience in the field of compliance, primarily within the financial industry. They started their career as a Compliance Officer at FBOP Corporation in 2002 and held this role until 2010. In 2010, Kellie joined Wintrust Financial Corporation as a Vice President of Compliance/CRA, a position they held until 2023. Following this role, they were promoted to Senior Vice President of Compliance at the same company. The specific end date for their current role is not provided.

Kellie Cunningham obtained a Bachelor of Arts degree in Economics and Psychology from the University of Michigan, where they studied from 1998 to 2002.