His ten goals in 19 appearances helped Keitrace FC gain promotion to the top tier of Liberian football, the First Division.

He led the team to the final of the 2015 Liberian First Division League season, where LISCR FC lost to Nimba United Football Club on penalty shootouts.

[2] Under the guidance of the Gambian coach Tapha Manneh, Jackson won his first league title, playing a key role in club's of longest unbeaten run in Liberian football.

[3] Jackson scored 13 goals in 25 appearances to help LISCR FC finish the 2016-17 league season unbeaten[4] and also winning the Liberian Cup to complete the double.

In early 2018, Jackson left LISCR FC and traveled to Belarus to attend tryouts with Belarusian Premier League club Shakhtyor Soligorsk.