Chief Underwriting Officer

About the role

The Chief Underwriting Officer will play a pivotal role in shaping the underwriting strategy and driving portfolio performance within a dynamic and rapidly growing organization. This executive will be responsible for defining how the company selects, prices, manages, and scales risk. The position requires a strategic operator who can partner effectively with the CEO and lead a team through a period of significant growth and change. The ideal candidate will have a strong background in medical stop loss underwriting and possess the ability to navigate high-pressure situations with professionalism and clarity.

Responsibilities

• Develop the company’s underwriting philosophy and risk appetite
• Design underwriting guidelines, referral authority, and pricing frameworks
• Establish underwriting governance and controls
• Define portfolio construction methodology
• Own underwriting profitability and portfolio performance
• Maintain key metrics, including loss ratio, renewal retention, quote conversion, premium growth, and underwriting margin
• Establish underwriting scorecards and reporting cadence
• Lead underwriting discussions with fronting carriers, reinsurers, and captive managers
• Support treaty design and underwriting compliance
• Build underwriting operating infrastructure and evaluate predictive analytics and pricing engines
• Partner with brokers and distribution leadership to establish the company as a credible underwriting partner
• Recruit and scale the underwriting organization while developing underwriters and analysts
• Build a culture of accountability and disciplined growth

Requirements

• 7+ years of underwriting experience in medical stop loss
• 5+ years of leadership experience
• Experience managing underwriting profitability
• Experience working with carriers, MGUs, reinsurers, or captives
• Experience building underwriting guidelines and operating processes
• Executive presence with the ability to engage in healthy debate and drive decisions
• Ability to underwrite $20-25 million per year personally
• Bachelor’s degree
• Captive underwriting experience is preferred
• Experience launching products or business units is preferred
• Familiarity with Milliman, Claros, Curve, AMS is preferred
• Executive-level leadership experience is preferred
• Actuary background or certification is preferred
• Degree in actuarial, mathematics, or statistics is preferred

Benefits

• Full medical coverage with a $5,000 HSA paid out bi-monthly
• Vision and dental insurance
• Life and supplemental life insurance
• Short-term and long-term disability coverage
• Flexible PTO (unlimited)
• Standard holidays and sick time rolled into PTO