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Senior Stop Loss Underwriter (Remote)

Daley And Associates, LLC
Hartford, CT Remote Full Time
POSTED ON 3/24/2026
AVAILABLE BEFORE 7/7/2026

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.

Compensation:

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

Role Responsibilities:

  • 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

Required Qualifications:

  • 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

Benefits & Perks:

  • Employer-sponsored health insurance

  • 401(k) retirement plan with company match


    For immediate consideration, please email your resume to Ellie Boyd at eboyd@daleyaa.com

Salary : $105,000 - $130,000

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