Winston Bennett

                    Winston  Bennett  BSc, CLU, CHFC

Winston Bennett

Winston Bennett is a graduate of Wolmer’s Boys’ School and the University of the West Indies. After working as the Plant Chemist and Production Manager of the Caribbean Steel Company, he entered the Life Insurance Industry as a sales representative.


As a salesman he qualified for nearly all industry awards and, after becoming a Senior Branch Manager, he managed one of the largest branches of Life of Jamaica (now Sagicor Life). Apart from being a repeated winner of his Company’s Unit Manager and Employee Benefits Trophies, he was on two occasions designated as the industry’s Branch Manager of the Year by the Life Insurance Managers Association of Jamaica (LIMGAA). Recently, Winston has been selected as the 2016 designate for the Caribbean Association of Insurance and Financial Advisors (CARAIFA) Hall of Fame.


After taking early retirement from Life of Jamaica, he worked as the Executive Sales Manager of Blue Cross of Jamaica and as a Sales Advisor for NCB Insurance. Presently, Winston is in full retirement but still spends time conducting sales seminars across a wide cross- section of Jamaican industries.


Winston has been widely used as a Congress Chairman, Master of Ceremonies and Motivational Speaker for the insurance and other industries in Jamaica and throughout the Caribbean. He is married to Dawn and they have two adult children and two grandchildren. His hobbies are hiking and horticulture.