Jacobson was the 24th overall pick in the 2008 MLS SuperDraft and the first pick by D.C. United. However, instead of playing in MLS, Jacobson signed a contract with Lorient of France’s Ligue 1. However, injuries limited his playing time, and he never played a first team game for Les Merlus.
Despite trialling with several clubs in Europe, Jacobson returned to MLS in 2009 and was allocated to the team which originally drafted him, D.C. United. He made his United debut as a substitute in DC's first game of the 2009 MLS season against Los Angeles Galaxy.[4]
Jacobson was traded to FC Dallas on February 18, 2011, in exchange for a second-round pick in the 2013 MLS SuperDraft.[6] He scored his first professional goal on May 28, 2011, while playing for Dallas against Houston Dynamo.[7]
After three and a half years served at the Texas club, Jacobson was traded to New York City FC for a third-round pick in the 2016 MLS SuperDraft,[8] becoming only their fifth ever player. As the new expansion club was not due to begin competitive games until 2015, he was immediately loaned out to Stabæk IF of the Tippeligaen in Norway to preserve his match fitness.[8] He returned to NYC for the 2015 season and appeared in 33 matches.
On March 11, 2016, NYC traded Jacobson to Vancouver Whitecaps FC in exchange for targeted allocation money.[9] Jacobson announced his retirement on January 17, 2018.[1]