Dan Foreman (Dennis Quaid) is a 51-year-old advertising executive and head of sales for "Sports America", a major sports magazine. Happily married with two daughters, Dan faces a life-changing event when his magazine is bought out by Globecom, an international corporation that promotes the corporate concept of "synergy". After he is forced to fire several of his longtime colleagues, Dan is demoted and becomes the "wingman" of his new boss, Carter Duryea (Topher Grace), a 26-year-old business school prodigy. While Dan develops clients through handshake deals and relationships, Carter champions the corporate creed of synergy, cross-promoting the magazine with the cell phone division and "Krispity Krunch", a snack food also owned by Globecom.