Jacobs was born and raised in Harrington Park, New Jersey, where he was educated at Northern Valley Regional High School, Old Tappan. Jacobs is the son of Rafael Jacobs, who works as a lawyer, and Marti Jacobs. He has a brother, Douglas Jacobs, who is the president of Integrated Sports Media, a sports firm, located in Hoboken. Jacobs is also a graduate of the Tisch School of the Arts. During a hiatus from the school in 1986, he worked as an assistant director to John Sayles on the independent film Matewan.

Jacobs has been active as an assistant director in his career for film directors such as the Coen brothers, Richard Linklater, Sayles, John Schlesinger and Steven Soderbergh. Jacobs first began cooperating with Soderbergh in 1993 on King of the Hill. In 2004, Jacobs released Criminal, his first feature film as a director, which he also wrote the script and helped produce. His second project was Wind Chill, announced in October 2005. It premiered in 2007. In March 2014, it was reported that Jacobs would helm Magic Mike XXL, the sequel to the first film, with Soderbergh acting instead as an executive producer, cinematographer and film editor.