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Senior Stop Loss Underwriter; Remote

Remote / Online - Candidates ideally in
Hartford, Hartford County, Connecticut, 06112, USA
Listing for: Daley And Associates, LLC
Remote/Work from Home position
Listed on 2026-02-12
Job specializations:
  • Insurance
    Underwriter, Insurance Analyst, Risk Manager/Analyst
Salary/Wage Range or Industry Benchmark: 85000 - 105000 USD Yearly USD 85000.00 105000.00 YEAR
Job Description & How to Apply Below
Position: Senior Stop Loss Underwriter (Remote - 105K)

Salary Range: $85,000–$105,000 + bonus/benefits.

A growing insurance organization is seeking a Senior Stop Loss Underwriter to join its expanding team. This is an exceptional opportunity to work in an entrepreneurial, collaborative environment with the stability of a larger organization.

What You’ll Do
  • Develop sound specific and aggregate stop loss pricing recommendations for prospective and inforce employer stop loss accounts
  • Analyze large claims datasets to identify medical expense drivers prior to nurse review
  • Partner with internal sales teams, brokers, TPAs, and clients to drive growth and implement successful plan designs
  • Participate in the sales process by providing underwriting guidance and strategy
  • Make independent underwriting decisions within authority limits while maintaining thorough documentation
  • Mentor junior underwriters, analysts, and trainees
  • Collaborate with administration to ensure audit compliance and adherence to underwriting policies
  • Maintain a profitable book of business aligned with departmental goals
What We’re Looking For
  • Minimum 5 years of experience in medical stop loss underwriting
  • Deep knowledge of healthcare payers, plan administration, and medical service providers
  • Strong analytical, risk management, and pricing skills
  • Exceptional organizational, time management, and attention to detail
  • Excellent communication and interpersonal skills, capable of collaborating with internal and external stakeholders
  • Comfortable in a fast-paced, evolving environment
Why This Role
  • Opportunity to lead and shape underwriting decisions for a growing portfolio
  • Work in a high-impact, entrepreneurial culture with strong leadership support
  • Competitive compensation, bonus, and benefits package
  • Meaningful role contributing to organizational growth and client success

Interested candidates are encouraged to send their resume directly to Kyle Archer at

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Position Requirements
10+ Years work experience
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