Whitaker received his bachelor's degree in political science and government from the University of Wisconsin-Whitewater. He then went on to receive his master's degree in accounting and finance from the University of Wisconsin-Madison and served an advisor to the Chancellor and Board of Trustees on the future of the university.
Active in the community, Whitaker currently serves as Chairperson of the Greater Mankato Growth (GMG) Board of Directors. GMG operates as the region’s Chamber of Commerce and Economic Development engine. He is also Chairperson of the Board of Directors of the Mankato Area Foundation Holdings, where he manages non-cash assets gifted to the foundation.