He was drafted by the Florida Marlins in the 7th round of the 1994 Major League Baseball Draft. He made his major league debut on March 3, 1998, for the Marlins against the Chicago Cubs. He set career-highs in games played, at-bats, home runs, and RBI that year. On April 9, 1999, he was claimed off waivers by the Seattle Mariners. Released after the 1999 season, he signed with the Tampa Bay Devil Rays and spent the entire year with Triple-A Durham. After the 2000 season, Jackson signed with the Detroit Tigers with whom he played for the next two seasons.
On November 6, 2002, Jackson signed with the Devil Rays and spent the whole year in the minors. In 2004, he played 16 games for the Atlanta Braves' Triple-A affiliate, the Richmond Braves.[4]
Jackson began his coaching career at the minor league level in the Cincinnati Reds' organization. In 2007, Jackson became the hitting coach for the Single-A Sarasota Reds, and again served as the hitting coach in 2008.[5] He was named the hitting coach for Double-A Carolina for the 2009 and 2010 seasons,[5] then he assumed the same position for the Triple-A Louisville Bats beginning with the 2011 season, under new manager David Bell.[6] He then served as the Reds' roving minor league hitting coordinator from 2012 through 2016.
In January 2019, he was named field coordinator for the Boston Red Sox' player development system.[7]
