Vice President, Health Insurance – Relocation to the Cayman Islands

We are currently seeking a seasoned and strategic Vice President to lead the group health insurance division of a well-established organization in the Cayman Islands - relocation required.

Vice President, Health Insurance – Relocation to the Cayman Islands.

This role requires the successful candidate to relocate to The Cayman Islands; associated relocation costs will be covered by the client.

We are currently seeking a seasoned and strategic Vice President to lead the group health insurance division of a well-established organization. This is a senior-level opportunity for a proven leader with deep experience in health insurance operations, strategic growth, and cross-functional team management.

In this role, you will oversee the performance, strategy, and day-to-day operations of the division, managing senior managers across Claims, Underwriting, Client Relations, and Service & Operations. You will also play a key role in shaping the future of the business through innovation, data-driven decision-making, and strong stakeholder engagement.

Key Responsibilities:

• Drive and implement the division’s strategic plan, aligning operational performance with long-term business goals
• Lead and develop a high-performing management team, including Claims Managers, Underwriting Managers, Service & Operations Managers, and Client Relations Managers
• Oversee underwriting and claims functions to ensure efficiency, accuracy, and regulatory compliance
• Monitor portfolio profitability, identify growth opportunities, and lead cross-selling initiatives
• Foster strong relationships with clients, providers, reinsurers, and internal stakeholders
• Ensure high-quality customer service outcomes and continuous process improvement
• Report on business performance and client outcomes to senior leadership
• Support compliance efforts and promote best practices across the division

Minimum Qualifications and Experience:

• 10+ years of senior-level experience in health insurance, with exposure to underwriting, claims, operations, and customer service
• Proven ability to lead diverse teams and manage multiple departments or functions
• Advanced degree (MBA or equivalent) and a recognized insurance designation (e.g., FLMI, CEBS, HIA)
• Strong financial and analytical skills, with a results-driven and strategic mindset
• Excellent communication and leadership abilities, with a collaborative approach to management
• Familiarity with leveraging technology to enhance business efficiency and service delivery