Stop Loss Underwriter (VP) - Insurance - Chicago - Hybrid

A leading organization in the insurance and risk solutions space is seeking a Vice President of Stop Loss Underwriting to lead underwriting strategy, profitability, and operational excellence for a growing large claims solutions business. This executive leadership role will oversee underwriting operations, pricing strategy, product innovation, and team development while partnering cross-functionally with actuarial, sales, claims, and senior leadership teams.

Responsibilities:

• Lead underwriting strategy aligned with profitability, growth, and risk management objectives
• Oversee stop loss underwriting, pricing, and risk assessment across complex medical risk programs
• Partner with sales and distribution teams to support business development initiatives
• Collaborate with actuarial and product teams on new product design and pricing structure
• Drive process improvements, underwriting optimization, and technology enhancements
• Build and mentor a high-performing underwriting team
• Ensure compliance with regulatory standards and internal underwriting guidelines
• Deliver reporting, analytics, and strategic insights to executive leadership

Qualifications:

• Bachelor's degree required, industry designations preferred 
• 10+ years of medical stop loss underwriting experience, including leadership responsibility
• Deep expertise in underwriting strategy, pricing methodologies, and risk evaluation

This is a high-impact leadership opportunity for an experienced underwriting executive seeking to shape strategy, drive innovation, and lead a growing stop loss underwriting platform. The expected salary range for this position is between $180K-$280K, depending on experience. Qualified candidates, contact Erin at esullivan@daleyaa.com for more details.