 In 2016, Naiboi was featured the songs "Gudi Gudi" by Kristoff and "Tingika" by Rankaddah, the two songs were successful and went on to win the awards for "Breakthrough Video" and "Best New Artist" respectively at the Pulse Music Video Awards (PMVAs).His 2017 single, "Problem", topped the music charts in Kenya and enjoyed heavy rotation on all the radio stations.In September 2018, Naiboi released the single “2-in-1”, a love song, which featured several East African celebrities recording videos of themselves ‘jamming’ to the song.