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Jonathon Winters has a total of 10 years of work experience. Jonathon first worked as an Account Manager at Pukka Headwear from December 2009 to November 2011, where they managed seasonal headwear and cold weather accessory programs for various partners. Jonathon then joined Totes Isotoner in November 2011 as an Associate Account Executive, responsible for growing private label, licensed, and branded accessory programs. In June 2013, they became a Business Development Manager at Totes Isotoner, specifically focusing on branded umbrellas, gloves, and slippers. From August 2015 to February 2020, they held the role of Account Executive at Totes Isotoner, handling Totes and Isotoner branded products for key accounts such as Kroger, Fred Meyer, Publix, Albertson's/Safeway, H-E-B, Wegmans, and Giant Eagle. Finally, they worked as a National Account Manager at Totes Isotoner from February 2020 onwards, with responsibilities including managing accounts with grocery stores and drug chains.

Jonathon Winters attended Kent State University from 2003 to 2004, where they studied Fashion Merchandising and Marketing, but did not complete a degree. Jonathon then went on to Bowling Green State University from 2004 to 2008, earning a Bachelor of Science degree in Apparel Merchandising and Product Development, with a focus on Marketing.