Senior Stop Loss Underwriter; Remote

Senior Stop Loss Underwriter (Remote)

A well-established insurance organization based in Hartford, CT is adding a Senior Stop Loss Underwriter to its underwriting team. This role is responsible for end-to-end pricing ownership of a stop loss portfolio, working cross-functionally with sales, program management, and senior leadership to support sustainable and profitable growth. Candidates within a 50-mile radius may work a 2-day hybrid schedule; otherwise, the position may be fully remote.

$105,000–$130,000 annually, depending on experience

• Independently underwrite and price Specific and Aggregate Stop Loss coverage for new business and renewals in accordance with established guidelines
• Analyze large-loss claims data to assess risk and identify primary medical cost drivers
• Collaborate with sales teams, brokers, TPAs, and internal partners to support client acquisition and retention efforts
• Advise clients and partners on plan design considerations and stop loss coverage options
• Exercise underwriting authority to make sound risk decisions while maintaining compliance standards
• Manage a profitable book of business while consistently meeting turnaround and service-level expectations
• Provide mentorship and technical guidance to junior underwriters and contribute to continuous process improvement

• 5+ years of medical stop loss underwriting experience
• Bachelor’s degree or equivalent combination of education and relevant experience
• Strong knowledge of healthcare funding arrangements, plan administration, and medical risk evaluation
• Advanced analytical, pricing, and underwriting decision-making capabilities
• Excellent written and verbal communication skills with the ability to build strong internal and external relationships
• Ability to perform effectively in a fast-paced, evolving environment
• Employer-sponsored health insurance
• 401(k) retirement plan with company match

For immediate consideration, please email your resume to Ellie Boyd at