After graduating from De La Salle College, he left for Liverpool, England to study sports science, pursuing a master's degree.
In 2009, Benstead was appointed as a youth manager for English side Tranmere Rovers.
One year later, he was appointed as a youth manager for English Premier League side Everton, and by 2013 was working as an analyst for the club.
In 2017, he was appointed as an analyst for English Premier League side Manchester United.
During his stay with the club, he worked under Portuguese manager José Mourinho and helped them achieve second place in the league and reach the 2018 FA Cup final.