CARAIFA’s 2016 Hall of Fame Inductee entered the Life Insurance business as a salesman with the St. Andrew Circle Branch of Life of Jamaica (now Sagicor) in 1976 after serving as the Plant Chemist and Production Manager with Caribbean Steel Company.
He has been a qualifier for most of the Industry’s top awards including the prestigious Million Dollar Round Table. He was appointed Unit Manager in 1981 and on 3 occasions won the Life of Jamaica Unit Manager’s Trophy. He was appointed Branch Manager in 1990 and Senior Branch Manager in 1993. He has repeatedly qualified for the Life Insurance Managers and General Agents Association (LIMGAA) Master Branch Award and was designated Branch Manager of the Year by LIMGAA in 1994 and 1995.
After taking early retirement from Life of Jamaica, he was appointed Executive Sales Manager of Blue Cross of Jamaica and later worked as a Regional Sales Manager and Training Officer for the National Commercial Bank Jamaica (NCB) Insurance. He currently serves as a Sales and Training Manager for Excel Insurance Brokers.
In his insurance career Winston has recruited/trained/managed approximately three hundred (300) insurance agents.
The holder of a BSc (Hons,) degree in Chemistry from the University of the West Indies, Winston became an Life Underwriters Association Training Course (LUATC) graduate in 1980, a Chartered Life Underwriter (CLU) in 1982 and a Chartered Financial Consultant (ChFC) in 1999.
A very involved member of the Insurance Industry, Winston has served as a Life Underwriters of Jamaica (LUAJ) now the Jamaica Association of Insurance and Financial Advisors (JAIFA) Board Member for over 5 years. He has also given yeoman service on several of the Association’s Committees. He served LIMGAA in the capacity of a Board Member and Congress Chairman. In the area of education, Winston was a member of the CLU Institute, and a moderator for both LUATC and Agency Managers Training Course (AMTC) Moderator.
His talent as an outstanding motivational speaker and Master of Ceremonies par excellence has made him a much sought after Main Platform Speaker for Sales Congresses. Congresses held in, Jamaica, Trinidad & Tobago, Barbados, Grenada, Dominica, Belize and Bermuda has benefited from this gift including a LIMRA Conference held in Jamaica in 2001. He has also been a Keynote Speaker for numerous Sales Awards, Retreats, Seminars and Conferences for several companies which include: Sagicor Life Jamaica, Jamaica Money Market Brokers (JMMB) Insurance, Demerara Life, Guardian Life Jamaica, Scotia Insurance and Allied Insurance Brokers.
Winston has been a much sought after Master of Ceremonies for matrimonial occasion, not only in the Insurance Industry but also in the wider corporate Jamaica recording a whopping 250 weddings.
Winston Bennett is deeply involved in both Church and Community Affairs. He serves as: Chairman of the Board of Elders of Covenant City Church, a leader in the Christian Community in Jamaica – serving on many boards, a leader of Deeper Life Ministries (DLM), and the inner city outreach programme of the schools and churches in Trench Town and Majesty Gardens in Kingston.
The 46 years union between Winston and his wife Dawn has been blessed with two children and two grand-children. His hobbies include hiking and horticulture.
As a result of his tremendous impact on professionals in the Insurance Industry throughout the Caribbean, his unflinching support of activities of the Caribbean Association of Insurance and Financial Advisors (CARAIFA), and involvement in activities that have served to enhance the image of the insurance professionals, CARAIFA is pleased to induct in its 2016 Hall of Fame Mr. Winston Bennett, BSc, CLU, ChFC.
