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Dale Shepherd has a diverse range of work experience. In 1987, they began their career at The Sharper Image as a Manager, where they oversaw the operation of two different locations in Chicago and served as a media spokesman. Dale then worked their way up to become a District Manager, responsible for multi-store retail management for thirteen years. After leaving The Sharper Image in 2008, Dale joined Human Touch, LLC as the Director of Field Retail Programs. In 2018, they were promoted to Senior Director, overseeing Direct & Online Sales Channels. Currently, Dale holds the position of Vice President, Consumer Sales at Human Touch, LLC.

Dale Shepherd's education history includes a Bachelor of Science degree in Communications from Southern Illinois University, Carbondale. Additionally, Dale has pursued further education at the Quinlan School of Business, Loyola University Chicago, where they have studied Organizational Behavior and completed a Master of Business Administration (MBA) degree. Further details regarding the start and end years of these educational experiences are not provided.