Transitioning from the streets to label suites, Sickamore has commanded high-ranking positions at several prestigious record companies.

In 2012, Sickamore began his tenure at Def Jam Records, where he quickly established himself as a genre-defining A&R with the success of YG and Jeremih. Just two years later, he was personally recruited by legendary music executive L.A. Reid to join Epic Records, where he helped craft the prolific career of new age hip-hop heavyweight Travis Scott, whose four studio albums all hold certified platinum status.