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Jason DeHaan has extensive work experience in various leadership roles, primarily as a Chief Information Officer (CIO). Jason has worked for Gildan since 2017, where they currently serve as the CIO. Prior to that, they worked for Abercrombie & Fitch from 2012 to 2017, leading the information technology organization for the company. Jason also served as the CIO for the City of Chicago from 2010 to 2012, and as the First Deputy CIO from 2007 to 2010. Jason DeHaan has also worked as the Chief Technology Officer for ieLogic from 2001 to 2006, and as a Manager in the Global Retail Practice at Accenture from 1996 to 2001. Jason started their career at the University of Illinois at Urbana-Champaign, where they worked as a Manager of Onsite Consulting from 1991 to 1996. Jason DeHaan began their professional journey as an intern at Chesterfield Federal Savings and Loan from 1988 to 1994.

Jason DeHaan attended Morgan Park Academy from 1980 to 1990, where they did not earn a specific degree or study a particular field. Jason then pursued a Bachelor of Science degree in Finance from the University of Illinois Urbana-Champaign, graduating in 1994. Following this, they attended Northwestern University - Kellogg School of Management from 2010 to 2012, where they earned an MBA degree.