Jackson coached Jada Harris to honorable mention All-America honors in high jump in 2019. He has produced ten NCAA East Region/NCAA Preliminary qualifiers: Brian Miller – high jump (2010), Stephanie Aguguo – triple jump (2011), Becky Stoyle - triple jump (2013, 2014, 2015) and Kelsey Crawford – javelin (2016), Kris Horn – high jump (2017) and Jada Harris – high jump (2019, 2021) & 100m hurdles (2019), and Lillian Kirry – 400m hurdles (2021) during his time at UMass.

Jackson has produced 39 Atlantic 10 champions, 22 New England Champions, and 25 new school records during his time at UMass-Amherst.

Prior to coming to UMass in 2009, Jackson spent the previous two years working with the University of North Carolina at Chapel Hill sprinters, women's pole vault and multi-event athletes, including three All-Americans and four ACC champions.

Before coaching at UNC, Jackson was the assistant men's and women's track & field coach at Roberts Wesleyan College in Rochester, N.Y., from 2004 to 2007. While at Roberts Wesleyan, he was responsible for working with the teams' sprinters, hurdlers, and relays. Jackson guided three members of the Raiders to NCCAA national titles and coached five NCCAA All-Americans.

From 1998 to 2003, Jackson worked as a software testing engineer for Heidelberg Digital and as a New York State public high school Section V track and field official. He also coached for the ACS Track Club and Nichols Academy and Churchville-Chili Sr. High, during his time in Rochester.

A standout discus thrower and sprinter in high school, Jackson went on to compete for Susquehanna University where he received all-conference accolades and earned a trip to the NCAA Division III national championship as a part of the school's 400m relay team in 1994. He graduated from SUNY Buffalo in 1998 with a Bachelor’s of Arts degree in Media Study and went on to earn a Masters of Arts in Organizational Communication from SUNY Brockport in 2000.