Jackson, who was among a group of players to be released by the Saddlers at the end of last season, has agreed a deal until January which includes an option to extend for the rest of the campaign.
The 31-year-old Canadian international, who penned a two-year deal with Jon Whitney's Walsall in the summer of 2016, struggled to find form during his time with the Saddlers, scoring just seven times in forty-nine fist-team outings, before being loaned out to League Two side Grimsby Town.
Jamaican-born Jackson has enjoyed a well-travelled career, which has seen him play for clubs such as Rushden & Diamonds, Gillingham, Norwich City, Eintracht Braunscwheig, Millwall, Coventry City, Barnsley, Blackburn Rovers, and the Saddlers.
Speaking about the move, Simeon said; "I'm delighted to be here and can't wait to get going. The lads have welcomed me in really well. It's happened really quick but it's been good. The manager was a great guy to meet and as soon as I met him I got a good feeling and I'm looking forward to working with him."