Having qualified as a Seaplane pilot after courses at Lee-on-Solent, Jolliffe spent all his brief flying career in seaplanes.
He became CO of 700 Squadron on 14 February 1942 whilst ashore at Dekheila, Egypt. The function of this squadron was to provide aircraft and aircrews to HM Ships fitted with catapults. The aircraft were mainly the disembarked flights from Mediterranean Fleet capital ships sunk or put out of action by U-boat or human torpedoes. In April 1942 six Walruses from the Squadron were sent to Beirut to provide inshore A/S patrols off the Levant coast. It seems likely that Jolliffe was with this unit when he was killed in a flying accident off the coast of Syria at sea on 3 June 1942.