VP, Stop Loss Underwriting (greater Chicago area) $285K base!

Vice President, Stop Loss Underwriting - Greater Chicago 

A growing and innovative organization in the healthcare insurance and risk solutions space is seeking a strategic and experienced Vice President, Stop Loss Underwriting, to lead and scale its underwriting function. This executive-level role will oversee underwriting strategy, profitability, pricing discipline, operational excellence, and team leadership across a sophisticated stop loss portfolio.

Base salary range: $200,000 – $285,000 annually

Key Responsibilities

• Lead the overall underwriting strategy for the stop loss business, aligning performance with profitability, growth, and risk management objectives
• Oversee underwriting operations for traditional stop loss insurance, gene therapy programs, and large claim solutions
• Partner cross-functionally with sales, actuarial, claims, product development, and executive leadership teams
• Develop and enhance pricing methodologies, underwriting guidelines, and risk evaluation frameworks
• Drive operational improvements through process optimization, technology enhancements, and scalable underwriting practices
• Lead, mentor, and develop a high-performing underwriting team while fostering a collaborative culture
• Support business development initiatives and strategic distribution partnerships
• Ensure underwriting compliance with all regulatory requirements and internal standards
• Analyze underwriting performance metrics and provide strategic reporting and recommendations to leadership

Qualifications

• 10+ years of medical stop loss underwriting experience and/or 15+ years of progressive underwriting experience with leadership responsibilities
• Must be able to be on-site 2–3 days per week
• Strong expertise in stop loss pricing, risk assessment, and underwriting strategy
• Proven leadership experience managing and developing underwriting teams
• Strong analytical, negotiation, and decision-making skills
• Experience implementing underwriting tools, technologies, and process improvements
• Advanced Excel and written communication skills required
• Advanced degree or equivalent experience in business, finance, actuarial science, or related field preferred

For immediate consideration, qualified and interested candidates should reach out to Kelly Lucey at klucey@daleyaa.com.

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