The Board of Directors of Cayman First Insurance Company is pleased to announce the appointment of Roger Balkissoon, the company’s former Technical Manager, to succeed Warren Rolle as Managing Director. Mr. Rolle returned to The Bahamas in June after being named Group Senior Vice President & Chief Operating Officer at Bahamas First Holdings, the ultimate parent company of Cayman First, based in Nassau. Concurrently, the Board also announced the promotion of Jonathan Welds to Technical Manager.
As Managing Director, Mr. Balkissoon will lead the Cayman First executive team and provide strategic and operational leadership to oversee the company’s growth and innovation plans.
Mr. Balkissoon joined Cayman First in 2019 as Technical Manager. He has 30 years of diverse industry experience in business development, technical underwriting, training and managing teams and leveraging technology for greater efficiency. His wealth of experience has been gained through his work in Canada, Trinidad and the wider Caribbean. He holds a BSc in Sociology and Management and is a Fellow of the Canadian Insurance Institute (FCIP). He was elected to the Board of Directors of the Insurance Association of the Caribbean (IAC) in 2021.
“We are fortunate to have Roger take the helm of Cayman First,” said Mr. Rolle. “His broad-based international experience in the insurance industry and extensive leadership across both the strategic and operational functions at the company make him the ideal choice to drive Cayman First forward in this challenging but exciting time. We worked closely together over the past few years and I am confident that he will provide continuity of purpose for the company. I look forward to seeing the continued growth of Cayman First under his leadership.”
Commenting on his appointment, Mr. Balkissoon said, “I am honoured by this opportunity to lead Cayman First during a time that holds great opportunity for growth. I am grateful for the confidence the Board has placed in me and I look forward to working alongside the executive team to build on our current momentum. I see a very bright future ahead and I am eager to continue the journey.”

Mr. Welds has 12 years of insurance experience and has been with Cayman First since 2017. He holds the Advanced Diploma in Insurance (ACII) from the Chartered Insurance Institute and is pursuing a Fellowship. He is also currently pursuing the Associate in Risk Management designation.
“Jonathan has worked with us for more than five years and his appointment demonstrates our company’s ability to develop outstanding leaders from within,” said Mr. Rolle. “He is an exceptional talent and his expertise will be key to driving our technical strategy, service and support for our customers and business partners.
Mr. Welds added: “I’m delighted to step into this new role that will ensure technical excellence remains at the heart of our business. I look forward to contributing to the growth of the company during this important time for our industry.”
About Cayman First Insurance Company
Cayman First is an industry-leading Property & Casualty and Health insurer delivering best-in-class products and services that meet the needs of individuals, households and businesses in Cayman. An integral player in the Personal and Commercial segments of the Cayman Islands insurance market since 1984, the company is regulated by the Cayman Islands Monetary Authority and by the Health Insurance Commission within the Cayman Islands Department of Health Regulatory Services. Cayman First has an AM Best financial strength rating of A- (Excellent) with a stable outlook. It has been part of the Bahamas First Group since 2010 and contributed US$67 million in premiums to the Group in 2021.
About Bahamas First Holdings Limited
Bahamas First Holdings Limited is a publicly traded company that carries out general and health insurance through its subsidiaries in The Bahamas and the Cayman Islands. It is the ultimate parent company of insurers Bahamas First General Insurance Company Limited and Cayman First Insurance Company Limited – which both hold an A- (Excellent) financial strength rating from AM Best – and registered insurance intermediary NUA Insurance Agents & Brokers Ltd. The Group reported Gross Written Premiums in excess of US$178 million on an overall basis in 2021.
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