While performing with the Bishops, Kenny worked as a part-time political advisor and consultant, helping run and manage local and regional political campaigns. In the fall of 2002 Kenny joined the campaign staff of U.S. Congressman
Ernie Fletcher. The following year the Congressman ran for
Governor of Kentucky and was elected to a four-year term. Kenny worked in the Fletcher administration as the executive director of the
Kentucky Governor's Mansion. During his tenure as executive director, Kenny helped establish the annual Easter Egg Roll at the Governor's Mansion in 2004. He also served as a member of the Historic Properties Advisory Commission , and on the board of the Governor's Mansion Preservation Foundation, a 501(c)(3) organization formed to raise funds for the renovation of Kentucky's executive residences. Kenny managed the multimillion-dollar renovation of Kentucky's executive residence that began in the winter of 2006. He was appointed by Governor Fletcher to the
Kentucky Arts Council and served on the board of the Kentucky Music Hall of Fame. After Fletcher's term in office, Kenny worked as Special Projects Manager for the Legislative Research Commission . In 2016 he went to work in the office of
Mayor Jim Gray in
Lexington, Kentucky as Deputy Communications Director and was appointed by Gray as the city's first LGBTQ Community Liaison. Kenny currently serves as Legislative Aide to 4th District City Councilmember Susan Lamb. Kenny has produced several high-profile events in the Kentucky State Capital, including the Gospel Celebration in commemoration of the Kentucky Governor's Mansion's centennial and the 2017 inauguration of Governor
Matt Bevin. ==Solo work==