Jeff Boles served on the Indianapolis 500 observer staff and joined the Indy Racing League as an official upon its formation in 1996.

[3] Boles served as assistant campaign manager and spokesman for Republican candidate Stephen Goldsmith in the 1991 Indianapolis mayoral election.

Boles left the office of Mayor Goldsmith and joined the ownership group, which included NFL Quarterback Jim Harbaugh, car dealer Gary Pedigo, motorsports executive John Barnes, and television producer Terry Lingner.

[14] He also created a motorsports consulting agency, Motorsportslaw.com and Motorsportsbusiness.com[15] In October 2010, Boles was hired as public relations director for Indianapolis Motor Speedway.

On July 9, 2013, Hulman company CEO, Mark Miles promoted Boles to President of Indianapolis Motor Speedway.

[18] Boles remained as President of Indianapolis Motor Speedway when Roger Penske purchased the track and IndyCar in November 2019.