Chester is a senior marketing representative at KHEAA, where he has worked 23 years. Before joining KHEAA, he spent eight years in admissions and financial aid at Union College in Barbourville, KY. Chester has held positions in both state and regional associations, including serving as KASFAA President in 2009-2010.
He and his wife, Jennifer, who is the financial aid director at Transylvania University in Lexington, KY, have been married for 12 years. Chester has one son, Tyler, who also lives and works in Lexington.