VP, Stop-Loss Underwriting — Hybrid Leadership

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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