Sherwood began his coaching career at Tottenham Hotspur, progressing from assistant first team coach to manager in a five-year spell, then managing the club from December 2013 to his dismissal in May 2014. He resumed his managerial career at Aston Villa in February 2015, taking them to that season's FA Cup final and saving them from relegation from the Premier League, until being sacked in October 2015. Sherwood was director of football at Swindon Town from November 2016 until June 2017.