Senior Underwriter

Position Overview

The Senior Underwriter - Captives & Stop Loss is responsible for underwriting, pricing, and managing complex medical stop-loss and captive insurance programs. This role combines advanced risk assessment with strategic collaboration across brokers, consultants, and captive program stakeholders to drive profitable growth.

The Senior Underwriter serves as a subject matter expert in alternative risk financing, supporting both new business development and renewal portfolio management while ensuring disciplined underwriting and strong client outcomes.

Key Responsibilities

Underwriting & Risk Assessment

• Evaluate and underwrite medical stop-loss submissions for self-funded employer groups and captive programs
• Assess risk using claims data, large claimant analysis, industry trends, and demographic factors
• Develop pricing, rates, and contract terms (specific and aggregate stop-loss) aligned with risk tolerance and profitability targets
• Analyze complex cases, including shock claims, lasers, and high-cost conditions
• Apply underwriting judgment to unique captive structures and layered risk arrangements

Captive Program Expertise

• Underwrite group and member-level risks within captive insurance programs (single-parent, group, and cell captives)
• Collaborate with captive managers, consultants, and reinsurers on program structure and performance
• Evaluate risk-sharing mechanisms, attachment points, and pooling strategies
• Monitor captive performance, including loss ratios, funding adequacy, and member participation
• Contribute to program design and enhancements to ensure long-term stability and growth

Broker & Client Engagement

• Partner closely with brokers, consultants, and producers to win and retain business
• Provide technical underwriting guidance and explain pricing, terms, and risk considerations
• Participate in finalist meetings, strategy discussions, and client presentations as needed
• Negotiate terms and structures to balance competitiveness with sound underwriting discipline
• Build strong relationships with key distribution partners

Portfolio Management

• Manage a block of stop-loss and captive business, ensuring profitability and retention
• Analyze renewal business, including claims experience, trend assumptions, and rate adequacy
• Identify deteriorating risks and recommend corrective actions (rate adjustments, lasers, plan changes)
• Monitor portfolio metrics, including loss ratios, rate changes, and retention

Analytics & Reporting

• Interpret complex datasets including claims files, utilization reports, and actuarial projections
• Collaborate with actuarial and analytics teams to refine pricing models and assumptions
• Maintain accurate underwriting documentation and compliance with internal guidelines
• Contribute to reporting on pipeline, renewals, and portfolio performance

Market & Product Development

• Stay current on industry trends, including self-funding adoption, captive growth, and emerging high-cost therapies
• Provide insights into product development, including innovative stop-loss structures and alternative funding solutions
• Support development of underwriting guidelines and best practices

Qualifications

Required

• 5-10+ years of experience in medical stop-loss underwriting
• Strong expertise in self-funded health plans and stop-loss structures (specific & aggregate)
• Experience underwriting or supporting captive insurance arrangements
• Deep understanding of claims data, large claimant risk, and healthcare cost drivers
• Proven ability to manage broker relationships and negotiate complex deals

Preferred

• Experience with group captives or alternative risk programs
• Exposure to reinsurance structures and relationships
• Background in actuarial, analytics, or finance (highly analytical underwriting approach)
• Familiarity with pharmacy (Rx) trends and high-cost specialty drugs
• Professional designations (e.g., HIAA, CEBS, or actuarial progress)

Key Competencies

• Advanced underwriting judgment and risk assessment
• Strong analytical and financial acumen
• Negotiation and deal-making skills
• Broker and client relationship management
• Attention to detail and disciplined decision-making
• Ability to operate in a fast-paced, growth-oriented environment

Success Profile

A successful Senior Underwriter in this space is a technical expert and strategic partner-someone who can confidently evaluate complex risks, structure competitive deals, and collaborate across stakeholders to grow a profitable stop-loss and captive portfolio.