Career
Amateur
Kiffe played for local side Santa Barbara Soccer Club prior to playing his high school soccer at San Marcos High School. He played for Santa Barbara City College in 2007 before transferring to the University of California Santa Barbara Gauchos from 2009 to 2011 to close out his collegiate career. Club career
Kiffe played with Ventura County Fusion from 2011 to 2014, eventually becoming team captain.
After seeing him play for the Fusion against Sacramento Republic Football Club in the 2014 Lamar Hunt United States. Open Cup, Sacramento Republic signed Kiffe for the remainder of the 2014 USL Pro season.