Fleming has been part of the FOX Stations Sales team since its inception. In 2019, he was promoted to SVP of FOX Stations Sales. Since 2004, Fleming had served as the Vice President and Director of Sales for FOX Stations Sales. Prior to that, he held the position of Vice President and General Sales Manager at FOX Stations Sales and, before that, Sales Manager. Previously, Fleming was the Vice President in charge of managing the sales team for FOX Television Stations. Earlier in his career, he served as an Account Executive and Team Sales Manager for Petry Television.