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Anthony W. Stefani has a diverse work experience. Anthony W. is currently a Village Trustee for the Village of Cary, Illinois. Prior to this role, they held various positions at ChanceLight Education, starting as the Vice President of Information Systems in 2008 and then progressing to the Senior Vice President of Information Technology, and finally the Senior Vice President of Information Technology & Facilities. Additionally, they founded R-Kyving and PowWow in 2016 and 2014 respectively. Anthony W. also served on the Board of Directors for the Rockford Foresters from 2009 to 2011. Earlier in their career, they worked as a Regional Trainer at Ombudsman Educational Services, a Business Educator at Paulding County School District, and in Training and Development at The Home Depot.

Anthony W. Stefani attended the University of West Georgia from 2004 to 2007, where they obtained a Bachelor of Science degree in Business Education. Anthony W. later attended Northwestern University from 2011 to 2012, specializing in Corporate/Business Analyst but did not earn a degree.