Chief Underwriting Officer

Boutique Recruiting

$150K — $250K *
Finance & Insurance
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7+ years of underwriting experience in medical stop loss
  • 5+ years of leadership experience
  • Proven track record managing underwriting profitability
  • Experience with carriers, MGUs, reinsurers, or captives
  • Strong background in developing underwriting guidelines and processes
  • Ability to underwrite significant portfolios ($20-25 million per year)
  • Bachelor's degree; actuarial background preferred

Responsibilities

  • Develop and implement the company's underwriting philosophy and risk appetite
  • Create underwriting guidelines and pricing frameworks
  • Establish governance and controls for underwriting practices
  • Define portfolio construction methodologies to enhance risk management
  • Oversee underwriting profitability and performance metrics
  • Lead discussions with carriers, reinsurers, and captive managers
  • Build the underwriting operating infrastructure to support analytics and pricing

Benefits

  • Full medical coverage with a $5,000 HSA contributed bi-monthly
  • Vision and dental insurance included
  • Life and supplemental life insurance coverage
  • Short-term and long-term disability insurance
  • Flexible PTO policy with unlimited time off
  • Overview of standard holidays and sick time integrated into PTO
Full Job Description
Position Title: Chief Underwriting Officer

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.

The Chief Underwriting Officer will lead the company's underwriting strategy, portfolio performance, operational infrastructure and team development. Reporting directly to the CEO, this executive will establish underwriting philosophy, drive profitability, oversee carrier and reinsurance relationships and build a scalable underwriting organization capable of supporting significant future growth.

Salary Range: $150,000 - $250,000 / Year DOE

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
  • Monitor 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

If you are a Chief Underwriting Officer looking to take the next step in your career, apply now! #LI-SG1

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