Saylor obtained his J.D. from the University of Victoria School of Law. He served as co-president of the Sports and Entertainment Law Society and competed in the 2022 New York Law School Negotiation Competition and 2023 Hockey Arbitration Competition hosted by the University of Toronto. He received a Bachelor of Arts in Political Science from Simon Fraser University after transferring from a small school in upstate New York.

Prior to law school, Saylor was a full-time hockey coach at various clubs in the lower mainland. In his free time, he enjoys playing and coaching hockey, golfing, and fantasy sports.