Meet The Team
Gerald Cruickshank
CARAIFA President
Trinidad and Tobago
Gerald began his career as an Insurance Agent with British American Insurance (Trinidad) in December 1989 at just 20 years old. He quickly moved up the ranks through dedication and hard work, becoming a Unit Manager in 1995 and then Agency Manager in 1997. Within a period of just six years, he expanded his agency from 19 to 64 agents and in addition to his St. Vincent Street, Port of Spain Trinidad office he opened a sub-office at TLH Building, Milford Road, Scarborough in Tobago.
Due to changes at his former company, Gerald took on the role of Agency Manager at Pan American Life Insurance (Trinidad) in July 2015 and continues to lead a dynamic team of advisors. His leadership extends to the Trinidad & Tobago Association of Insurance and Financial Advisors (TTAIFA), where he served two terms as President from 2015 to 2017 and again from May 2021 to May 2023, he now serves as the Immediate Past President of TTAIFA. Currently he is the President of the Caribbean Association of Insurance and Financial Advisors (CARAIFA) headquartered in Jamaica for the 2025-2027 term.
His contributions to the industry have earned him numerous awards, and he actively participates in annual company conventions and CARAIFA congresses. He enjoys travelling, supporting his football team Manchester United, and caring for his dogs, plants, and kitchen garden. His guiding motto, “Service is Key Always,” reflects his unwavering commitment to exceptional customer service. Gerald believes in giving back and is always trying to assist under-privileged kids in his township believing that all they need is a chance to do great things.