Olsen has also written songs for singers such as Craig Morgan, Garth Brooks, Dallas Smith, Rascal Flatts, The Judds, Kip Moore, and Kevin Borg.

[4] Later that year, he released his major-label debut single, "Raised by a Good Time", which was certified Gold by Music Canada in August 2015.

[5] In 2021, Olsen signed a joint record deal with Universal Music Canada and The Core Entertainment,[6] and released the extended play Relationship Goals,[7] which included the 2021 CFL Song of the Year, "What You're Made Of".

[8] In early 2023, he released the single "Outta Yours" and joined the Canadian leg of Old Dominion's "No Bad Vibes Tour" as an opening act.

[12] In August 2023, he released the single "Out Here" concurrently with the announcement of his new distribution deal with independent label Starseed Records.