Tilley originally participated in cycling before a knee injury forced him to quit the sport, and he began kart racing at the age of eight.

In 2015, he and co-driver Jerry Kaufman won a 13-hour endurance race at Virginia International Raceway sanctioned by the Sports Car Club of America.

[9] Tilley and Kaufman continued to drive together in the 2017 Pirelli World Challenge SprintX GTS class for The Racer's Group, where they finished second in the championship.

The project was spurred after Tilley befriended tech company businessman Dwight Merriman, with whom he started worked as a touring car racing driver coach in 2018.

[15] Era Motorsport's debut came at the 2020 24 Hours of Daytona, in which the team ran an Oreca 07 for Tilley, Merriman, Ryan Lewis, and Nicolas Minassian.

[19] The duo also entered the 24 Hours of Le Mans for IDEC Sport alongside Jonathan Kennard;[20] despite Merriman crashing in practice and being replaced by Patrick Pilet for the race, the car finished 15th.

[27] Tilley began dabbling in stock car racing in May 2021 when he joined Live Fast Motorsports for the NASCAR Cup Series' Texas Grand Prix at Circuit of the Americas.