Senior Captive Underwriter

Position Summary

The Senior Captive Underwriter plays a critical role in evaluating, structuring, and pricing captive insurance programs. This individual will lead underwriting efforts for complex captive opportunities, collaborate with internal and external stakeholders, and contribute to the strategic growth of Crumdale’s captive portfolio.

• Lead underwriting for new and renewal captive programs, including group, single-parent, and cell captives
• Analyze risk profiles, claims data, and actuarial reports to develop pricing models and coverage structures
• Collaborate with actuarial, sales, and legal teams to ensure alignment on program design and execution
• Present underwriting recommendations to internal committees and external clients
• Maintain underwriting guidelines and ensure compliance with regulatory and internal standards
• Participate in building and evaluating alternative cell risk management strategies
• Mentor junior underwriters and contribute to training initiatives
• Support business development efforts by participating in client meetings and industry events

• Bachelor’s degree in Risk Management, Finance, Actuarial Science, or related field; CPCU, ARM, or similar designation preferred
• Minimum 7 years of underwriting experience, with at least 3 years in captive underwriting
• Ability to propose creative underwriting solutions
• Strong analytical skills and proficiency in Excel and underwriting software
• Excellent communication and presentation skills
• Proven ability to manage multiple complex projects in a fast-paced environment
• Deep understanding of stop loss, self-funded plans, and captive structures

• Innovative and entrepreneurial culture.
• Competitive compensation and benefits.
• Opportunities for professional growth and leadership.
• Collaborative team environment focused on delivering client value.

At Crumdale, we strive to provide a comprehensive and supportive benefits package to ensure the well-being of our employees. Our benefits include:

• Medical
• Telemedicine
• Dental
• Vision
• Life, AD&D, Disability
• 401(k)
• Flexible Time-off

Please note: Crumdale Specialty is not engaging with external recruitment agencies; please refrain from contacting us regarding this position.