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.

Senior Underwriting Manager – P&C

The Role: The Senior Underwriting Manager – P&C is responsible for the strategic leadership, operational oversight, and performance management of all Property & Casualty (P&C) underwriting functions across the organization. This includes Broker business, Direct underwriting operations, Retention activities, and regional branch underwriting teams.

Job Responsibilities:

• Lead P&C underwriting strategy across all channels, aligning risk appetite, profitability, and growth objectives.
• Monitor portfolio performance, market trends, and underwriting results to drive profitability and underwriting excellence.
• Establish underwriting guidelines, controls, and reporting to support disciplined decision-making and strategic oversight.
• Provide leadership of underwriting operations, ensuring consistent standards, service excellence, and regulatory compliance.
• Build and maintain strong relationships with brokers, intermediaries, and key clients to enhance service and market presence.
• Oversee treaty and facultative reinsurance programs to optimize capacity and support underwriting objectives.
• Lead treaty negotiations, renewals, and compliance with reinsurance reporting requirements
• Support complex risk placements, renewals, and business development initiatives to drive growth.
• Use market intelligence to inform underwriting strategy, pricing, and product development.
• Other related duties and responsibilities as assigned by management.

Requirements

Qualifications & Experience

• Bachelor’s degree in Business Administration, Risk Management, Finance or a related field.
• Holds Dip CII designation or higher.
• A minimum of 5 years in a management capacity overseeing a Property and Casualty Underwriting department with the ability to align underwriting decisions to profitability, growth, and risk appetite objectives for all lines of business.
• Experience overseeing reinsurance treaty and facultative programs to optimize capacity and support underwriting objectives.
• Excellent communication and relationship management skills with brokers, clients, and reinsurance partners.
• Leadership and people management skills, with experience developing high-performing teams and driving accountability
• Strong communication and stakeholder management skills, including the ability to present insights to senior leadership and the Board
• Advanced analytical and data-driven decision-making skills, with the ability to interpret KPIs, trends, and portfolio performance.

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$120,000 – CI$160,000 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 Senior Underwriting Manager – P&C position, please visit Cayman First’s careers page on our company website and submit your application to the Senior Underwriting Manager – P&C opening here: www.caymanfirst.com/careers. WORC Portal ID: J3R8U8- Senior Underwriting Manager – P&C