Beginning his political career in his native Mississippi, Stevens worked on Thad Cochran’s campaigns and others. Stevens worked for Bob Dole's 1996 presidential campaign and was part of George W. Bush's media team in 2000 and 2004. His book The Big Enchilada is a chronicle of Bush's 2000 campaign. He and Russell Schriefer worked for John McCain's campaign early in the 2008 election, but changed their allegiance to Mitt Romney by July 2007. Overseas, Stevens worked successfully for two candidates in 2005 and 2006. In Albania he worked for Prime MinisterSali Berisha during the 2005 election campaign, where he based the campaign primarily on "a pledge to reduce corruption". He also worked for 2006 election campaign of Joseph Kabila in the Democratic Republic of the Congo. He has served as strategist and media consultant to dozens of Congressman, Governors and Senators. Notable clients include President Bush, Governor Romney, Governor Haley Barbour, Governor Tom Ridge, Senator Thad Cochran, Senator Dick Lugar, Senator Mel Martínez, Senator Chuck Grassley, Senator Roger Wicker, Senator Jon Kyl, Governor Bill Weld, Governor Paul Cellucci, Governor Bob Riley and others. In 2010, Stevens served as strategist and media consultant to 3 winning senate campaigns: Rob Portman in Ohio, Roy Blunt in Missouri and Dan Coats in Indiana. In 2011-2012, Stevens was the lead strategist in Governor Romney's Presidential campaign. He is credited with developing the strategy that won the primary. In 2014, Stevens helped Senator Thad Cochran win the Mississippi Senate race which included overcoming primary challenger Chris McDaniel. During the 2014 election cycle, Stevens and his business partnerRuss Schriefer saw all of their clients win their general election campaigns including Governor Larry Hogan in Maryland and Elise Stefanik - the youngest woman ever elected to congress.
Stevens emerged from an internal power struggle during Romney's 2008 presidential campaign, in which he and Schriefer clashed with the campaign's existing media team, to become Romney's senior strategist in 2012. In that role he was responsible for the campaign's focus on employment, its efforts to help Romney connect with voters, and its aggressive primary campaign against Rick Perry. Stevens and Schriefer also handled advertising for the campaign.
Controversy
Stevens was publicly criticized by numerous Romney campaign officials, according to a widely cited Politico article published on the evening of September 16, 2012 but largely overshadowed by the 47% comment in the 2012 Romney video leak the following day.
2016 U.S. presidential election
Stevens was one of the most prominent Republicans to oppose Donald Trump in the 2016 presidential election predicting Trump would be defeated in the election.
Television and film
Stevens has worked on television shows including Northern Exposure and I'll Fly Away. He consulted on the 2011 Hollywood film The Ides of March and was a Fellow of the American Film Institute.