Jerry has spent over 30 years creating advertising for hundreds of notable local, national and global brands. Starting his career as an art director for the Chicago White Sox, he helped create the 50th anniversary All-Star Game poster at Comiskey Park. Moving on to Campbell Mithun as an art supervisor Jerry spent six years working on Kroger and Corona Beer.

In 1990 Jerry co-founded DiMeo-Rosen Partners making the Chicago White Sox their first client, followed by the Chicago Bulls, Chicago Bears, Arlington International Racecourse, The Second City and Wendy's to name a few. The agency gained popularity by creating such campaigns as the White Sox’s 'Good Guys Wear Black' Bo Jackson's 'Hip Season Ticket Plan', and the Chicago Bulls 'Most Valuable Ticket in Town.' Jerry sold his interest in 1996 to start The Rosen Group with clients Gingiss Formalwear, Frank Thomas's Big Hurt Enterprises, and helped launch Major League Soccer team the Chicago Fire. The agency changed its name to ENRE@CH in 2011 and merged with The Plum Tree Group, transitioning into a fully integrated digital marketing platform attracting clients such as Drees Homes and The Black Ensemble Theater.

Jerry has won over 40 advertising and marketing awards and has been recognized in the NY Times, Chicago Tribune, Sun-Times, Adweek and Age Age. He has served as Chairman of the Frank Thomas Charitable Foundation and is currently Vice Chairman of Worldwide Partners, Inc.