Senior Underwriting Manager at Cayman First

Level: Senior
Posted: Jun 4, 2026

Description

Cayman First, an industry-leading Property & Casualty and Health insurer, is seeking a Senior Underwriting Manager - P&C. This role involves strategic leadership, operational oversight, and performance management of all Property & Casualty underwriting functions, including Broker business, Direct underwriting operations, Retention activities, and regional branch underwriting teams.

Required Skills

Underwriting Strategy
Portfolio Monitoring
Underwriting Guidelines
Underwriting Operations Leadership
Relationship Building
Reinsurance Program Oversight
Treaty Negotiation
Risk Placement Support
Market Intelligence Utilization

Additional Information

Required Previous Experiences: overseeing a Property and Casualty Underwriting department
Experience overseeing reinsurance treaty and facultative programs
Preferred Qualifications: 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.