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Dennis Wheeler has a diverse work experience spanning over several years. Dennis began their career as a Deputy Municipal Attorney at the Municipality of Anchorage in 1998, where they served until 2003. From 2003 to 2005, Dennis worked as an Assistant Attorney General for the State of Alaska, providing legal representation to state officials in various matters. Following this, they joined the Regulatory Commission of Alaska as an Advisory Section Manager from 2005 to 2009. Dennis then served as a Municipal Attorney at the Municipality of Anchorage from 2009 to 2015. In 2015, they held the position of Managing Member at Wheeler & Associates LLC, and also worked as an HR Director, Contracts Administrator, and Senior Project Manager at Resource Data, Inc. during the same period.

Dennis Wheeler completed their Bachelor's Degree in History from the University of Oregon in the years 1986 to 1989. Dennis then pursued further education and obtained a Juris Doctor (J.D.) degree from Willamette University College of Law between 1990 and 1993. Prior to their college studies, Dennis attended Chugiak High School, although the specific timeframe is not provided.