Despite Jackson's earlier vow to move into management, he became an SFA agent representing players including fellow Scots Jackie McNamara, Mark Wilson and Steven Thompson. In February 2013, Jackson relinquished his agent status to join client and former Celtic teammate McNamara – recently appointed as manager of Dundee United – as a coach. While at the club, United lost the 2014 Scottish Cup and 2015 Scottish League Cup Finals. Jackson left Dundee United in September 2015, following McNamara's departure. Three months later he was declared bankrupt. He then served as assistant manager to Gary Locke at Raith Rovers, until both were sacked by the club in February 2017.