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Jimmy Kleager has a diverse work experience, starting in 2010 with attending the Army Command and General Staff College, where they earned a Masters in Public Administration. Jimmy then worked as a Battalion Operations Officer, planning and conducting counterinsurgency and stability operations in the Kandahar Province of Afghanistan. Jimmy later served as a Brigade Operations Officer for a Stryker Brigade Combat Team, managing training and resources during a time of Government Sequestration. In 2014, they became a Future Plans Officer for Headquarters Special Operations Command. In 2019, they joined Man Made as a Coach and Trainer, helping men achieve their full potential in various aspects of their lives. Currently, they hold the position of Managing Director at Coldwell Banker Distinctive Properties, in addition to being a Licensed Associate Real Estate Broker.

Jimmy Kleager obtained their Bachelor of Science degree in Biology/Biological Sciences, General from Colorado State University, where they attended from 1992 to 1997. Later, in 2010, they pursued a Masters degree in Public Administration with a concentration in Leadership from Central Michigan University.