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Stop Loss Underwriter (Remote!)

Daley and Associates, Hartford, CT, United States


An insurance company located in Hartford, CT, is seeking a Stop Loss Underwriter to join its growing team. You’ll own pricing for a block of stop loss business while partnering closely with sales, programs, and leadership to drive profitable growth. This role can be fully remote or a 2-day hybrid option (if within 50 miles).

Compensation: $85,000-105,000 + bonus

Responsibilities

Price Specific and Aggregate Stop Loss for new and renewal employer groups in line with underwriting guidelines

Evaluate large claims data and identify key medical cost drivers

Partner with sales, brokers, TPAs, and internal stakeholders to support growth and retention

Consult clients on plan design and stop loss coverage strategies

Make independent underwriting decisions within authority limits

Maintain a profitable, compliant block of business and meet service timelines

Mentor junior underwriters and contribute to underwriting best practices

Qualifications

3+ years of experience in medical stop loss underwriting

Strong understanding of healthcare payers, plan administration, and medical risk

Advanced underwriting, risk assessment, and analytical skills

Excellent communication, organization, and relationship-building abilities

Comfortable in a fast-paced, evolving environment

Strong benefits package, including

Employer-paid health insurance

401(k) with company match

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