Fountain began his career with the Department of Corrections in 2002 as a felony supervision officer in District 18. In 2004 he transferred to District 17 as a misdemeanant supervision officer. Fountain was promoted to assistant supervisor of the District 9 Lexington field office in 2007. He transferred to District 19 in 2008 where he was instrumental in initiating the PORTAL program. He also served on the Newburg Weed and Seed Steering Committee and the Newburg Justice Reinvestment Pilot Re-entry Program.

In 2012, Fountain transferred to District 17 where he continued his involvement in the Shawnee/Newburg Justice Reinvestment Program. He was also a volunteer with the Justice Reinvestment Beautification and Community Garden project, which allowed participants to give back to Louisville's Newburg area. In 2011, Fountain was the recipient of a Commissioner's Award for his re-entry program participation and volunteerism. Fountain is a 2002 graduate of the University of Louisville, where he earned a Bachelor of Science degree in justice administration. He is also a 2007 graduate of the Commissioner's Executive Leadership Development Program.