Jay began his career under the Matthews' umbrella in 2002 at South Side on Lamar where he worked as an administrative assistant and landlord assistant for the artist residency program. In 2003, he was transferred to a new Matthews project just up the street from South Side to what became Gilley's Dallas. He began working on day two of the project as Assistant to the General Manager. Since then, Jay has worn several hats at Gilley's, including Office Manager, IT Manager, Group Sales Associate, Event Sales Manager, and Assistant General Manager. He was promoted to General Manager in June of 2011 and continues to promote growth for Gilley's Dallas as well as all of South Lamar Street.