MEDICAL STOP LOSS UNDERWRITER / SENIOR UNDERWRITER

Confidential; Chicago (IL); Hybrid; USD 65,000 - 140,000; Full time

Job summary

Join a forward-thinking organization that is revolutionizing the captive insurance model. This role offers the opportunity to work remotely or in a hybrid capacity from Chicago, IL, while playing a crucial part in shaping underwriting solutions. You'll evaluate submissions, analyze claims data, and determine coverage levels, all while collaborating with a dynamic team. If you have a passion for risk management and a background in health insurance, this position provides a unique chance to contribute to an innovative company focused on operational excellence and member empowerment.

Qualifications

• 2–5+ years of experience in health insurance or medical stop-loss underwriting.
• Strong understanding of risk management, healthcare costs, and claims analytics.

Responsibilities

• Evaluate medical stop-loss insurance submissions for group captive programs.
• Analyze historical claims data, health trends, and risk exposure for potential policyholders.
• Collaborate with internal teams to ensure underwriting aligns with regulatory standards.

Skills

Health Insurance Underwriting

Risk Management

Claims Analytics

Medical Terminology

Regulatory Compliance

Analytical Skills

Education

Bachelor's degree in Business

Bachelor's degree in Finance

Bachelor's degree in Insurance

Bachelor's degree in Mathematics

Job description

Note : This employer is open to candidates who want to work remote.

Medical Stop Loss Underwriter / Senior Underwriter

Location : Remote or Chicago, IL (Hybrid Option Available)

Compensation : $65,000 – $140,000 (depending on experience level as we are hiring for multiple level positions)

About the Role

Join a market-leading, member-owned group captive organization that's redefining the captive insurance model. Known for their innovation and commitment to strategic guidance, risk management, and operational excellence, this team is expanding rapidly. We are hiring multiple Medical Stop Loss Underwriters at various experience levels to support ongoing growth. You'll play a key role in shaping the future of captive insurance by providing tailored underwriting solutions that empower members with control and cost savings.

What You’ll Do

Evaluate medical stop-loss insurance submissions for group captive programs

Analyze historical claims data, health trends, and risk exposure for potential policyholders

Determine appropriate coverage levels and pricing for individual and aggregate stop-loss policies

Review group health plans, member demographics, and claims experience to identify high-cost claim risk

Collaborate with internal teams to ensure underwriting aligns with regulatory and compliance standards

Prepare underwriting documentation and contribute to strategy development for the program's profitability

What Makes You a Great Fit

2–5+ years of experience in health insurance or medical stop-loss underwriting

Strong understanding of risk management, healthcare costs, and claims analytics

Knowledge of medical terminology, regulatory issues, and insurance compliance

Proven analytical and problem-solving skills

Bachelor's degree in Business, Finance, Insurance, Mathematics, or a related field

Experience with pricing, stop-loss product structures, and cost-containment strategy is a plus

65,000 – $140,000 depending on experience

Bonus Potential based on individual and company performance

Flexible Work Arrangement : Fully remote or hybrid from Chicago, IL office

Benefits Package

Interested in working from home? This employer is open to candidates who want to work remote.

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