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Dean Olson's work experience starts with their current position as Chief of Staff at Contruent since 2022. Prior to that, they served as a Board Member at IPRO from 2021 to 2022. From 2019 to 2022, Dean was a Senior Associate at ParkerGale Capital. Before that, they worked as an Associate Consultant at Bain & Company from 2017 to 2019. In 2016, they gained experience as a Financial Services Intern at EY. Dean also worked as an Intern at Thomson Reuters in 2014. Dean began their career as a Caddie at Glen Oak Country Club from 2008 to 2013.

Dean Olson attended Glenbard West from 2009 to 2013, where they obtained their High School Diploma. Dean then went on to attend Indiana University Bloomington from 2013 to 2017, although the specific degree and field of study they pursued during this time are unknown.