After several years working with producers and teams in a variety of roles (including Ray Tobey and Stewart Bonn on the early combat flight simulator Skyfox), he began producing his own titles in the late 1980s.
In 1990, he was the producer of John Madden Football for the fast-growing Sega Genesis, a game developed by Troy Lyndon and Michael Knox of Park Place Productions, and co-designed by Scott Orr, the game that we still recognize today as Madden Football, the best-selling title in the history of games in North America.
A team member of the Madden team, Scott Orr joined Hilleman later at EA full-time in 1991 where both Hilleman and Orr were promoted to senior management roles in EA product development over the following few years.
Hilleman was later named Vice President in charge of Production for the company.
Rich Hilleman worked for Electronic Arts as Chief Creative Officer until May, 2016.