Dale grew up in Essex, where he attended Ashdon County Primary School and Saffron Walden County High School.
Dale was Research Assistant to the Conservative Member of Parliament Patrick Thompson, 1985-87, Public Affairs Manager for the British Ports Federation 1987-89, Financial Journalist with Lloyd's List 1989-90, and then Deputy managing director of the Waterfront Partnership & managing director of the Waterfront Conference Company 1990-96.