The son of ex-Gillingham manager Andy Hessenthaler, the hard-working and tough-tackling midfielder played almost 500 senior matches in a decade at EFL level. He is a former Chelsea youth who first signed for Gillingham in 2013, going on to win the club’s young player of the year. 

Across more than five seasons at Priestfield, he racked up in excess of 180 appearances in League One. Hess spent the next five years in League Two with Grimsby Town and Crawley Town before signing for Dagenham in 2023. He signed for the Fleet in summer 2025.