Wylie has worked on the coaching staffs of multiple teams in the Canadian Football League (CFL) and National Football League (NFL), including stints at the Oakland Raiders and the Cleveland Browns, both under head coach Hue Jackson.

[1] He also coached the offensive lines of the Winnipeg Blue Bombers and the Saskatchewan Roughriders of the CFL.

Under his coaching, center Jeremy O'Day, and guard Gene Makowsky were named CFL All-Stars.

On January 22, 2010, Wylie was named an assistant offensive line coach for the Denver Broncos.

On April 1, 2014, Wylie was named the offensive line coach for the Winnipeg Blue Bombers.

[12] In 2018, Wylie was featured on HBO's Hard Knocks with the Browns, a television series produced by NFL Films.