Underwriting Program Manager – Stop Loss (Fully Remote or Hybrid – Hartford, CT Area) A growing insurance organization based in Hartford, CT is looking to add an experienced Underwriting Program Manager to oversee a dedicated block of Specific and Aggregate Stop Loss business. This is a key leadership role with ownership over pricing strategy and underwriting results, offering the opportunity to make a real impact within a collaborative, entrepreneurial environment. The position can be fully remote, with a hybrid option (2 days onsite) for candidates located within 50 miles of Hartford. Compensation: $130,000–$160,000 base salary Responsibilities: Evaluate case information and risk factors to develop competitive and sound pricing recommendations for both new and in-force Specific and Aggregate Stop Loss accounts, in alignment with underwriting guidelines. Review large claim data in advance of clinical review to identify potential high-risk drivers and determine appropriate next steps. Build and maintain strong working relationships with sales partners, brokers, TPAs, underwriters, and other internal and external stakeholders. Advise clients and partners on stop loss structures and plan design considerations to ensure appropriate risk protection. Partner with the sales team throughout the quoting process to help position proposals competitively and strategically. Exercise independent underwriting authority while ensuring complete and accurate file documentation. Analyze submissions that fall outside standard guidelines and prepare well-supported exception recommendations for senior leadership review. Present clear risk assessments, financial impact analysis, and strategic rationale to support executive decision-making. Review, approve, or decline cases within authority, while offering guidance and alternative structuring recommendations to team members. Oversee assigned program workflow to ensure timely turnaround and balanced distribution of work across underwriting staff. Identify and evaluate key medical cost drivers impacting both new business and renewal accounts. Provide input to senior leadership on enhancements to underwriting guidelines, policies, and best practices. Mentor and develop underwriting team members to strengthen technical expertise, risk evaluation skills, and overall performance. Deliver ongoing coaching and structured feedback to drive consistent service standards and productivity. Partner with administrative teams to ensure documentation supports audit readiness and compliance requirements. Manage the portfolio to achieve targeted profitability and performance objectives. Qualifications: Knowledge and understanding of healthcare payers, health plan administration, and medical service providers. Bachelor’s degree or equivalent industry experience 10+ years of medical stop loss underwriting experience Prior leadership experience (3+ years managing or mentoring underwriters preferred) Strong knowledge of stop loss pricing, risk evaluation, and healthcare cost drivers Proven ability to lead teams while partnering effectively with sales and external stakeholders Strong analytical and decision-making skills Highly organized with the ability to thrive in a fast-paced setting What’s Offered Competitive base salary Employer-paid health insurance 401(k) with company match Flexible remote or hybrid work options For immediate consideration, please email your resume to Ellie Boyd at eboyd@daleyaa.com.
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