After college, Jason began puting in work as a sideman to many of the area's great musicians. Musicians Jason has accompanied include Frankie Avalon, Frank Foster, Rene Marie, Chris Calloway, The Four Aces and dozens more. The Jason Jenkins Group made it recording debute in 2009 with the album, Synchronicity featuring pianist Toru Dodo. 2010 saw the follow up recording Scenic Roots featuring Tenor Sax giant Charles Owens.
The Jason Jenkins Trio has been featured in several publications and has played in music venues nationwide. The group currently has a weekly residency, Saturdays at The Barrel Thief Cafe (Richmond, Virginia). 2012 Jason and jazz consort, Alan Parker launched 32 Bar Records, a record label dedicated to producing the works of regional jazz artists and showcase a variety of unsung talents from Virginia and beyond(32BarRecords.com). The label will feature Jason's 2012 release, The Cole Porter Songbook.