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Courtney Winkler has a diverse work experience spanning various industries. Courtney has held the role of Owner at The Loft at 36 Eleven since February 2023 and at 36 Eleven DIY & Decor since November 2020. Prior to their entrepreneurial ventures, Courtney worked as the Director of Retail Operations at HOMAGE starting in October 2015. Courtney previously held the position of Purchasing Manager at Mad River Harley-Davidson from January 2013 to March 2014. Before that, they worked as an Administrative Assistant/ Sales Manager at Norwalk Precast Molds from April 2011 to October 2012. Courtney also worked as an Area Manager at Aeropostale from April 2005 to April 2011.

Courtney Winkler attended Vermilion High School from 1998 to 2002. No specific degree or field of study information was provided.