Senior Underwriter

We are seeking an experienced Senior Medical Stop-Loss Underwriter to join a rapidly growing insurance organization. This role is responsible for evaluating, pricing, and underwriting medical stop-loss risks for self-funded and level-funded health plans, including captive and traditional arrangements. The Senior Underwriter will independently manage cases from initial evaluation through proposal development, assess financial exposure, and collaborate with leadership to support profitable underwriting decisions.

The ideal candidate has at least 5 years of medical stop-loss underwriting experience, strong analytical skills, and the ability to independently manage complex cases in a fast-paced environment. This individual is technically proficient, adaptable, and comfortable working within a growing organization where collaboration, accountability, and problem-solving are essential.

• Evaluate, price, and underwrite medical stop-loss coverage for self-funded and level-funded employer health plans
• Independently manage approximately 10–20 underwriting cases per week, from initial review through proposal preparation
• Analyze claims experience, financial exposure, group demographics, and risk factors to determine appropriate pricing and coverage terms
• Underwrite traditional and captive medical stop-loss arrangements
• Prepare accurate underwriting proposals and present recommendations for final review and approval
• Collaborate with carriers, managing general underwriters (MGUs), reinsurers, and captive partners
• Monitor underwriting profitability and support strategies that maintain a balanced and profitable portfolio
• Utilize underwriting software and analytical tools to evaluate risk and improve efficiency
• Contribute to the development and refinement of underwriting guidelines, processes, and internal systems
• Work closely with actuarial and operations teams to support business growth and underwriting accuracy
• Adapt to evolving business needs while maintaining quality, accuracy, and productivity

• Bachelor's degree required
• Minimum of 5 years of medical stop-loss underwriting experience
• Demonstrated experience independently underwriting medical stop-loss cases from initial evaluation through proposal development
• Strong understanding of self-funded health plans, stop-loss pricing, risk assessment, and underwriting profitability
• Experience working with insurance carriers, MGUs, reinsurers, or captive programs
• Ability to manage approximately 10–20 underwriting cases per week independently
• Strong analytical, mathematical, and problem-solving skills
• High level of technical proficiency and ability to learn new underwriting platforms
• Proficiency with Microsoft Office and underwriting-related technology
• Strong communication skills and ability to collaborate effectively across departments
• Adaptability, professionalism, and a solutions-oriented approach in a growing business environment
• Experience with captive underwriting preferred
• Familiarity with Milliman, Claros, Curve, or agency management systems preferred
• Background in actuarial science, mathematics, statistics, or related disciplines preferred
• Actuarial certifications, licensing, or coding experience are a plus

• Medical, dental, and vision insurance
• Employer-funded Health Savings Account (HSA)
• Life and supplemental life insurance
• Short-term and long-term disability coverage
• Monthly performance-based bonus opportunities
• Annual performance bonus opportunities
• Equity participation opportunities
• Flexible, unlimited paid time off
• 12 paid holidays
• Hybrid work environment with flexibility based on experience and business needs
• Strong emphasis on work-life balance