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Jonathan Winebrenner has extensive experience in the field of human resources and operations management. Jonathan currently serves as the Director of Human Resources at Congressional School since July 2022. Prior to this, they held the same position at Mandarin Oriental Hotel Group from November 2011 to June 2022. Before that, they served in various roles at The Greenbrier, including Director of Human Resources, Director of Labor Relations and HR Administration, Senior Operations Manager, and Conference Service Manager. Jonathan also worked as the General Manager at Boca Bay Pass Club and as the Hotel Operations Manager at The Greenbrier. Earlier in their career, they held the role of Manager of Restaurants and Banquets at The Greenbrier.

Jonathan Winebrenner attended Mercersburg Academy from 1982 to 1986, although the information does not mention any degree or field of study. Subsequently, they pursued a Bachelor of Science degree in Government at William & Mary from 1986 to 1990.