After college, Shapiro began working at ESPN and ABC Sports. He was responsible for the production of the documentary, SportsCentury. a comprehensive retrospective of the people and events that shaped the face of sports in North America over the past 100 years. Between 1997 and 1999 Shapiro was the executive producer of the series, which received an Emmy and Peabody Award as well as an Excellence in Sports Journalism Award from the Northeastern University's Center for the Study of Sport in Society. Shapiro became senior vice president and general manager of programming in 2001 and then executive vice president for programming and production in 2002. In 2003, Entertainment Weekly named Shapiro one of 2003's rising stars in entertainment. He secured new properties for ESPN and acquired rights to Monday Night Football, Wimbledon and the NBA. Beginning in 2002, ratings on ESPN rose for 10 straight quarters. He was the executive producer for Tilt, Dream Job, and Playmakers. Playmakers was awarded a 2003 American Film Institute award for TV Program of the Year, and the GLAAD Media Award for Outstanding Drama Series in 2004. During his tenure, the network was awarded a number of Emmy awards and an additional Peabody. He was also the recipient of the UJA-Federation of New York 2005 Sports for Youth Award and in 2006 he was again honored by the federation in the Broadcast Cable category. Shapiro was named to the Sports Business Daily40 under 40Hall of Fame in 2005 after being named to the list in 2002, 2003, and 2004. Shapiro left his position of executive vice president of programming and production at ESPN in May 2005. From October to December 2005, Shapiro was the CEO of Red Zone LLC as the company pushed for control over Six Flags. Once Red Zone solidified control over the company, Shapiro became Director, President, and Chief Executive Officer of Six Flags, with a tenure lasting from August 2005 until May 2010. Six Flags tenure was marked by a decision to market the theme parks to children and families instead of just targeting teenagers and young adults as the parks had attracted in the past. Shapiro also was a partner with Tom Cruise in the actor's production company, and was an executive producer of the 2008 United Artists film Valkyrie. Shapiro became chief executive officer and an executive producer of Dick Clark Productions in May 2010. While there, he was involved with the expansion of the company's programming format. Shapiro left the position of CEO soon after the sale of the company to Guggenheim Partners in 2012. After working as an advisor for Silver Lake Partners and William Morris Endeavor during the latter's acquisition of IMG. Following the acquisition, Shapiro's role was made permanent, becoming Chief Content Officer. He was then named co-president of WME-IMG in November 2016. In the Same year, Variety named him to its New New York Power List. Shapiro is also the co-owner of the new Los Angeles FC MLS franchise. He was the executive producer of the HBO series, Being Serena which was honored with a Producers Guild Award for Outstanding Sports Program.
