Kammala wannan jumla: Vail ya fara horo a shekara a lokacin da yake ƙaramin shekara a makarantar sakandare. Daga nan sai ya tafi Jami'ar Jihar Oklahoma inda ya kasance shugaban kungiyar NCAA ta 2009 Cross Country National Championship. Nan da nan bayan kammala karatunsa daga Jihar Oklahoma, Vail ya sanya hannu kan kwangila tare da Brooks Sports. Vail ya halarci Gasar Wasannin Olympic na 2012, inda ya kasance mafi girma. Vail kuma shine babban dan wasan Amurka a 2013 New York Marathon, kuma a
2014 London Marathon, inda ya gama 10th a 2 '10' 57, mafi kyawunsa.