[3] Dewsnip trained as a PE teacher, attending the Carnegie College of Physical Education for four years,[3] which later became part of Leeds Beckett University.
[5] He later taught at New Heys Comprehensive School, where two of his former pupils, Karl Robinson and Jim Bentley, would later become managers in the Football League.
[3] Dewsnip had worked at the Everton Academy for 17 years, coaching future England national football team internationals Wayne Rooney, Ross Barkley, Leon Osman and Jack Rodwell,[6] before leaving in July 2013 to work for the Football Association, initially as the technical lead for the England under-17 to under-21 teams.
[12] In December 2023, with the club in the EFL Championship, Dewsnip, supported by first team coach Kevin Nancekivell, took on caretaker manager duties, following the departure of Steven Schumacher to Stoke City.
[15] Following Ian Foster's sacking on 1 April 2024, Dewsnip, again supported by Kevin Nancekivell, was re-appointed as caretaker manager until the end of the 2023–24 season.