Randolph was born in January 1965 shortly before the death of his great grandfather, Sir Winston Churchill. After attending Harrow, Randolph undertook a short service commission in the Royal Navy and served as Gunnery Officer of HMS Alderney in the coastal protection squadron. On completion of the Navigating Officer Course he was appointed Navigator of HMS Swallow in the Hong Kong Squadron and promoted to Lieutenant. Subsequently, Randolph attended Buckingham University where he was awarded a degree in Financial Management and Accountancy, before joining Deloitte and Touche where he qualified as a Chartered Accountant.
In 1995 Randolph joined Lazard Asset Management, becoming Director of the Charities Division. In 2000 Randolph joined Schroder Private Bank and in 2003 he moved to Rathbones where he is an Investment Director managing investments for private individuals and foundations.
Randolph is a Trustee of the Winston Churchill Memorial Trust, Honorary Fellow of Churchill College Cambridge, Director of the Armed Services Charities Advisory Company (that oversees the investment for over 100 service charities) and Trustee of the Churchill Centre UK and US. He is also a Patron of JAGS, Winston's Wish, Gallipoli & Dardanelles International and London Legacy which supports Australian service families. Randolph is a regular speaker at Churchill conferences and dinners. Randolph and his wife Catherine have four children and live close to Sir Winston's home at Chartwell in Kent.