Roland Kesterson felt the call to preach at the age of 14. In 2001, he began his singing career with a bluegrass gospel group billed as Set Apart, serving as the lead singer and emcee. In 2008, Kesterson left Set Apart and began a preaching and singing ministry. He joined the Troy Burns Family to sing baritone in November of 2014. He became the baritone for the Inspirations in October of 2015.
After the restructuring of the Inspirations in 2017, Kesterson became the group's bass guitar player with the occasional vocal feature. In 2018, long-time Inspirations lead singer Matt Dibler left the group, and Kesterson took over lead singing duties.