 In 2018, Jackson signed with MSG Western New York to be an analyst for its weekly postgame series, "Bills Tonight".Along with fellow Bills alumni Brian Moorman and Terrence McGee and other prominent Buffalo figures, Jackson operates SEAR, a high-end steakhouse located within The Avant in downtown Buffalo.In October 2018 Jackson teamed up with Codes Socks LLC to create a Signature Series Sock that will benefit a local charity called UB HEALS.