About Cayman First: ‘First’ is more than our name, it’s our nature. Cayman First is an industry-leading Property & Casualty and Health insurer, delivering best-in-class products and services to respond to the changing needs of individuals, households and businesses. Through our carefully selected network of agents and brokers, we provide protection for our customers today and prepare them for a brighter tomorrow. Cayman First maintains an A- (Excellent) financial strength rating from global credit rating agency AM Best.

Vice President – Group Insurance Services

The Role: The Vice President – Group Insurance Services is responsible for the strategic leadership and overall performance of the group life and health insurance portfolio, including underwriting, claims, customer service, operations, and profitability.

Job Responsibilities:

• Develop and execute strategic business initiatives that drive sustainable growth, profitability, and operational excellence.
• Lead business transformation efforts by optimizing processes, leveraging technology, and strengthening organizational performance.
• Oversee financial and operational performance, including budgeting, pricing strategy, risk management, and key performance metrics.
• Provide leadership across underwriting, claims, customer service, and provider relations to ensure effective service delivery and sound risk management.
• Build and maintain strong relationships with clients, brokers, providers, reinsurers, regulators, and other key stakeholders.
• Monitor market trends, regulatory developments, and emerging opportunities to support informed business decisions and long-term competitiveness.
• Foster a high-performance culture through strong leadership, talent development, accountability, and continuous improvement.
• Other related duties and responsibilities as assigned by management.

Requirements

• Bachelor’s Degree in business, finance, insurance, economics or related from a recognized college or university.
• One advanced professional designation in life or health insurance, such as the FLMI, CEBS, HIA or equivalent.
• Minimum ten years’ experience at the management level in health insurance overseeing underwriting, claims, operations, and customer care.
• Excellent leadership and interpersonal skills at all levels, including with cross-functional teams.
• Excellent oral and written communication skills.
• Knowledge of and familiarity with health technology solutions.
• Strong knowledge of the Cayman Islands laws and regulations for health insurance.

Benefits

This is a full-time position at our George Town office and our office hours are Monday-Thursday (8:30am-5:00pm) and Friday (8:30am-4:30pm). The salary range is CI$130,000 – CI$170,000 depending on experience and qualifications. Cayman First offers a wide variety of benefits such as a comprehensive health insurance plan, pension plan, performance-based bonus, paid vacation, personal days, relocation assistance (if applicable), access to an employee assistance plan, paid maternity and paternity leave.

The closing date for applications on our website is July 8, 2026, and qualified Caymanians are strongly encouraged to apply for this exciting opportunity!

To apply for the Vice President – Group Insurance Services position, please visit Cayman First’s careers page on our company website and submit your application to the Vice President – Group Insurance Services opening here: www.caymanfirst.com/careers. WORC Portal ID: V2U3C2 - Vice President – Group Insurance Services