Ross attended the University of Illinois at Urbana-Champaign, before going on to work for SMY Media, Ogilvy and Mather, True North Media, and MediaMixNet. Over his 34-year career, he has worked on many accounts, including: American Airlines, Sears, Coors, and SC Johnson.

His hobbies range from traveling to cooking, and he was a Scottish Highland dancer for 12 years. One of his many accomplishments is having served for 10 years on the Chicago Broadcast Advertising Club board, before becoming the President of the board for 2001.