Oliver, grandson of Sir Austen Chamberlain, was born at Tonerspuddle, Dorset in 1950 and educated at Milton Abbey School and the Royal Agricultural College Cirencester. He qualified as a Chartered Surveyor 1976 and was made a Fellow in 1988. After an initial spell in general practice, Oliver spent 20 years employed as a Resident Land Agent responsible for property in Dorset and Yorkshire. Then, in 1996, established a small rural consultancy practice in Dorset, specialising in rural estate management in Dorset, Wiltshire and Hampshire.
Oliver joined the Territorial Army in 1972 and, following various regimental appointments, commanded the Royal Wessex Yeomanry from 1990 to 1994. Subsequently, he held a number of Staff appointments, including Colonel Yeomanry and Deputy Commander 43 (Wessex) Brigade. Oliver was appointed ADC to HM The Queen 1998 – 2000 and awarded the Queen’s Volunteer Reserves Medal (QVRM) 2004. Oliver is a Deputy Lieutenant of Dorset, Liveryman and Past Master of the Worshipful Company of Cordwainer. He is involved in a number of military and local charities. Other interests include his two Flatcoated Retrievers, country sports, walking, and skiing. Oliver is married to Georgina and they have two daughters and two grandchildren.