After retiring from football, Terry worked as an agent for six years before joining Richie Wellens at Oldham Athletic as the first-team coach in November 2017. After leaving in January 2018, Terry returned to Yeovil in the summer of 2018 to take up a role in manager Darren Way's coaching staff. Terry Joined West Bromwich Albion as the loan manager for the club in July 2019 to oversee the development of youth and first-team players leaving the club on loan. Terry was charged in November 2020 by the F.A. for breaching Rule E8 pertaining to betting, where it is alleged Terry placed 209 bets between 1 November 2017 and 25 October 2019.