Senior Captive Underwriter

About Crumdale Specialty :

Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. We optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees.

At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. Our company culture is rooted in alignment, innovation, and integrity.

About the Role:

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.

Key Responsibilities:

• 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

Requirements

• Bachelor’s degree in Risk Management, Finance, Actuarial Science, or related field; CPCU, ARM, or similar designation preferred
• Minimum 3-5 years of underwriting experience, with at least 1 year 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

Why Join Crumdale Specialty?

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

Benefits

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.