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Derrill Wakefield's work experience begins in 1997 at The Longaberger Company, where they worked as the Director of Information Technology - Applications Development. Derrill then moved on to Kichler Lighting in 2005 as the Director of Business Process Improvement. In 2007, they joined Sterling Commerce as the Director of IT Business Applications. From 2008 to 2010, Wakefield worked at The Goodyear Tire & Rubber Company in various IT leadership roles, including Global IT Director and PMO Department Manager. Derrill then joined GE Current, a Daintree company, in 2019 as the Director of IT Enterprise Application Services. Most recently, in 2022, Wakefield became the Vice President and Chief Information Officer at Christian Healthcare Ministries.

Derrill Wakefield has a Bachelor of Science degree in Manufacturing Engineering Technology from the University of Nebraska at Omaha. Derrill also holds a Master of Business Administration (M.B.A.) degree from the Wisconsin School of Business, with a focus on Business.