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.

Risk Analyst

The Role: The Risk Analyst is responsible for performing risk assessments, portfolio analysis, and technical pricing evaluations to support underwriting decisions and financial performance. Develops pricing models, Power BI dashboards, and management reports to monitor profitability, identify emerging risks, and support data-driven strategies. Ensures data integrity, regulatory compliance, and effective collaboration across departments.

Job Responsibilities:

• Extract, validate, reconcile, and maintain renewal datasets, ensuring accuracy, consistency, and data integrity.
• Prepare and reconcile SIF and Stamp Duty payment reports, ensuring accuracy and compliance with statutory requirements.
• Evaluate health insurance portfolio trends, claims experience, and profitability metrics to identify emerging risks and recommend corrective actions.
• Develop and maintain complex risk-based pricing models to assess premium adequacy, renewal performance, and underwriting profitability.
• Design, develop, and maintain Power BI dashboards and advanced pricing models to support performance monitoring and strategic decisions.
• Analyze and report on Gross Written Premium (GWP), claims, insured lives, loss ratios, and other key financial and underwriting metrics.
• Prepare and validate reinsurance and third-party provider reports, ensuring data accuracy and adherence to reporting requirements.
• Partner with internal departments to resolve data discrepancies, address operational queries, and improve reporting processes.
• Achieve monthly performance objectives while ensuring timely delivery of analytical reports and operational requirements.
• Present pricing analyses, portfolio insights, and risk-based recommendations to support underwriting and pricing decisions.
• Monitor departmental KPIs, identify opportunities for process improvement, and contribute to operational efficiency and business objectives.
• Other related duties and responsibilities as assigned by management.

Requirements

Qualifications & Experience:

• Bachelor’s degree in Accounting, Mathematics, Statistics, Actuarial Science, Finance, Data Analytics, or a related quantitative discipline.
• Professional certification in Life or Health Insurance through LOMA, HIA, or an equivalent recognized institution is highly desirable.
• Experience in the health insurance industry, with strong knowledge of underwriting principles, technical pricing, risk assessment, and portfolio management.
• Strong quantitative and analytical capabilities, including financial modelling, data validation, claims analysis, trend evaluation, and profitability assessment.
• Sound understanding of insurance policy structures, underwriting guidelines, regulatory requirements, and contractual documentation to support risk-based decision-making.
• Proficiency in insurance administration and underwriting systems, including data management, reconciliation, reporting, and analytical processes.
• Excellent communication, organizational, and problem-solving skills, with the ability to present technical findings, manage competing priorities, and consistently meet reporting deadlines.

Benefits

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$65,000 – CI$85,000 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, access to an employee assistance plan, paid maternity and paternity leave.

The closing date for applications on our website is November 20, 2026, and qualified Caymanians are strongly encouraged to apply for this exciting opportunity!

To apply for the Risk Analyst position, please visit Cayman First’s careers page on our company website and submit your application to Risk Analyst opening here: www.caymanfirst.com/careers. WORC Portal ID: D8K3H4– Risk Analyst.