Ray has been in the insurance industry since starting college in 1986. Ray worked for Kentucky Central/Kentucky National Insurance Company while attending the University of Kentucky. After finishing school, with a BS in communications, he went to work full time for Kentucky National Insurance as a supervisor in the home office.

In 1993, Ray was promoted to territorial manager of the Eastern Region of Kentucky. In 1996, Ray left the company side of the insurance business and joined what was then Hoffman, Ison & Greene, in Mount Sterling as a partner. The agency has seen several changes since 1996 and now operates in Mount Sterling, KY, and Paris, KY, under the umbrella of Limestone Agency.

Ray is a past president of the Professional Insurance Agents of Kentucky and was also a three-term chairman of the CIC/Education Committee for the PIAK. Ray obtained his Certified Insurance Counselor designation in 1994. Ray has served with Big I-Kentucky (Largest insurance agent association in Kentucky) on the board of directors since 2013 and was chairman of the board from 2019-2021.

Having grown up on a farm in Bethel, KY, the fourth son of A.T. and Dorothy Robertson, Ray felt at home moving to Mount Sterling in 2000 with his family. Ray and Stephanie Spence Robertson were married in 1994 and have two children. Ashlyn Ray Robertson (1998) is currently a doctorate of physical therapy student at the University of Saint Mary in Leavenworth, KS. Laken Scott Robertson (2000) is a senior at the University of Kentucky.

Ray is active in the community by serving First Christian Church as a deacon and committee chair, by being president of the Mount Sterling Main Street Board, and coaching youth baseball. In 2009, the Montgomery County Parks and Recreation Commission honored Ray with the Austin Adams Coach of the Year Award. Traditional Bank, a large community bank based in Mount Sterling, named Ray to the board of directors in 2006, and now he is a member of the Regional Bank Board of Traditional Bank. Ray also began serving as chairman of Longview Cemetery in 2018.