The son of a television writer, Ken Stein began his career in entertainment in various production assistant capacities for the musical and comedy variety series Rowan & Martin's Laugh-In. After the show ended its run, Stein was hired as a production supervisor on the children’s game show, Junior Almost Anything Goes. Not long after beginning his duties, Stein was promoted to stage manager, which allowed him to join the DGA in 1976. This subsequently led to additional opportunities and Stein was hired by CBS to stage manage the game shows The Price is Right and Password which started a long professional relationship with fellow stage managers Robert Chic and David Wader. Throughout his 40-year career, Stein has worked as a stage manager on pageants, game shows, award shows, talk shows, competition programs and musical specials including: Miss USA Pageant, Miss Universe Pageant, Miss America Pageant, Academy Awards, Primetime Emmy Awards, Grammy Awards, American Music Awards, ESPY Awards, Golden Globe Awards, NAACP Image Awards, People’s Choice Awards, MTV Video Music Awards, Billboard Music Awards, Nickelodeon’s Kids’ Choice Awards, Dancing with the Stars, The X-Factor, America’s Got Talent, Randy Jackson Presents: America's Best Dance Crew, American Idol, Jimmy Kimmel Live, The Tonight Show, and the Jerry Lewis MDA Labor Day Telethon.
Stein’s work on the Jerry Lewis telethon introduced him to showman Ed McMahon who brought him on as stage manager for the long-running musical and performance competition series Star Search where he stayed throughout its entire run. Another mainstay of his career has been working on various pageant competitions. He has even turned down jobs that conflict with the pageant schedule. Traveling the world as a stage manager, Stein was given the nickname “Mr. White Gloves” by contestants and crewmembers alike for wearing bright white gloves while orchestrating the various stage movements during a pageant production. Not limiting himself to reality and musical variety, Stein has also worked as a stage manager for the scripted series Full House, Mr. Show, Sunset Beach, and Beyond Belief: Fact or Fiction.