n 2010 Diamond joined the Dancehall music group Don Dem.[6] Don Dem released two projects. In 2011, "Loaded Mixtape" and In 2013 "The ReMixtape".[3] In 2014 Kirk Collaborated with "T.G." a.k.a "Tommy Gunn" to release the single, Dem Nuh Real under the "Armzhouse" label in "Jamaica".[7]
In 2015, Kirk and Bob Da Builda of Don Dem were nominated for a Juno Award for the single Love Inna We Heart which was produced by France based "Galang Records".[4] In 2016 he traveled to Jamaica to collaborate with Derrick Morgan on a remake of the latter's 1960s song "Conqueror".[8]
With high anticipation for the release of Diamond's solo debut EP entitled,Greater. Kirk flew to the UK to promote the project in 2017. The final stop on the media run was to BBC Radio 1Xtra where he joined Seani B on his program. What was to be a normal interview, ended up being much more when Kirk delivered a well-received freestyle.[9][10][5] After returning to Canada, Kirk took on the festival circuit starting with the Grace Jerk Festival in Toronto,[11] and the Reggaefest in Calgary, Alberta.[12]
In 2018 the EP, "Greater" won the Juno Award for Reggae Recording of the Year.[13][14] 2018 is also when Diamond would emerge as one of the most sought after performers in Canada, performing at over 72 shows including the "Love Thy La