[8][9] Jackson started playing in bands around the 6th grade moving from bassist to guitarist and singer in high school.

[10] He met Aaron Sharp while attending university in Southern California and they created Saint Motel around 2007.

[12] Saint Motel released the full-length album Voyeur, whose tracks reached the top of the Hype Machine Charts in 2012, and an EP, My Type, which includes two international alternative top 40 singles written by Jackson, "Cold Cold Man" and the platinum-selling single, "My Type".

[13] In 2015, Jackson led Saint Motel and dancers at the Coachella Valley Music and Arts Festival,[14] as one of the stops on the band's US tour.

[15][5] In 2016 the band released its second full-length album, saintmotelevision, featuring the single "Move" which Jackson stated he wrote while they were on tour in Germany.