Cayleb has been on staff with GTFC Impact since January 2019. He is currently the women's assistant at Ohio Northern University. Prior to taking over the women's assistant position at Ohio Northern University in December 2018, he spent the previous four seasons as an assistant coach for the Ohio Northern University men's soccer program. Cayleb served as the assistant coach for the men's and women's program at Defiance College from 2012-2014, where he also earned his Master's of Arts in Education with a concentration in Sport Coaching. Cayleb graduated in 2011 from Wilmington College where he was a member of the men's soccer program and graduated with an undergraduate degree in Health and Physical Education with a coaching minor.