Underwriting Program Manager - Stop Loss; Fully Remote or Hybrid - Hartford, CT

Overview

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.

• 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.

• 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

• 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