On February 14, 2015 Whitesides released his second EP A Piece of Me, including previously released single "Words".
In May 2015, BMG announced their partnership with Whitesides and the formation of his label, Double U Records, where he serves as CEO. In August 2015, he was named Radio Disney's "Next Big Thing" featured artist.
On October 21, 2015, he performed his single "Secrets" on Good Morning America, his network morning TV debut. He released his third EP (second of original material) Faces on Film on October 23, 2015.
On December 3, 2015, Spotify announced him as one of the next big artists to look out for in 2016.
Jacob grew up in Tennessee with his mother, Becky, and his younger sister, Sierra. Whitesides dated fellow The X Factor contestant and performer Bea Miller in April 2015. The couple broke up in May 2016 after a year of dating.