Jason has collaborated with artists such as Sara Groves, Andrew Peterson, Joel Hanson (frontman for 90s Christian rock band PFR), Andy Gullahorn, Randall Goodgame, Jason Ingram, Thad Cockrell, Andy Osenga (of Caedmon's Call) and others. He has toured with Jeremy Camp, Sanctus Real, Matthew West, Shawn McDonald, downhere, Big Daddy Weave, The Afters, Mark Schultz and others.

Jason has won two ASCAP Performance Awards for "More Like Falling in Love" (2011) and "Good to Be Alive" (2012).[citation needed] He has shared the stage with many major artists such as Michael W. Smith, Steven Curtis Chapman and Sanctus Real. His first No. 1 single, "Nothing Is Wasted", reached the top spot on the Soft AC Chart in May 2013 and remained there for nine weeks. His release in 2012, was named Album of the Year by critics and garnered three Top 5 radio singles which included the "Nothing Is Wasted" single. Also in May 2013, he was honored at ASCAP's 35th Annual Christian Music Awards with the "Most Performed Song Award" for his song "Good to Be Alive" co-written with Brandon Heath and Jason Ingram. The song was a Top 5 single on Christian radio and was released on Gray's album A Way to See in the Dark.