Director, Stop Loss Underwriting

Questpro; Cincinnati (OH); On-site; USD 150,000 - 230,000; Full time

Job summary

Questpro in Cincinnati seeks a seasoned Technical Director of Medical Stop Loss Underwriting to lead risk selection, set underwriting guidelines, and steward profitability across blocks. This role reports to the Division VP and requires deep expertise and a proven profitability track record.

You will manage facultative reviews, audit distribution partnerships, and coordinate with compliance, actuarial, and risk leaders.

Qualifications

• Bachelor’s degree preferred or strong education in related field.
• 5–10+ years of experience within Medical Stop Loss underwriting.
• Proven profitability track record in stop loss portfolios.
• Ability to negotiate complex financial deals and communicate assessments to executives and partners.
• Proficiency with underwriting platforms and data analysis tools.

Responsibilities

• Risk Selection & Facultative Reviews: evaluate risks to ensure profitable new business and high-margin retention.
• Partner & Broker Management: manage relationships with MGUs, TPAs, and specialty brokers for pricing and placement.
• Audit & Compliance: conduct annual risk-based underwriting audits of distribution partners.
• Profitability Monitoring: analyze loss ratios and financial reports to identify trends.
• Reinsurance Coordination: review programs to identify opportunities and expansions.
• Stakeholder Alignment: report to executives across compliance, actuarial, and risk.

Skills

Risk assessment

Underwriting

Negotiation & influence

Data analysis

Stakeholder communication

Education

Bachelor’s Degree

Job description

Technical Director, Medical Stop Loss Underwriting

Position Overview

We are seeking a seasoned, highly technical Medical Stop Loss Underwriting Director to evaluate risk, drive block profitability, and manage key distribution partnerships. Reporting to the Division VP this role operates as a senior individual contributor focusing on executing facultative reviews, managing underwriting guidelines, and conducting risk-based audits of distribution partners. The ideal candidate will possess a stellar track record of managing loss ratios and negotiating complex risk placements with external and internal stakeholders.

Responsibilities

• Risk Selection & Facultative Reviews: Evaluate and select medical stop loss risks to ensure profitable new business acquisition and high-margin retention of in-force blocks through detailed facultative assessments.
• Partner & Broker Management: Cultivate strategic relationships with MGUs, TPAs, and specialty brokers to manage daily business strategy, pricing, terms, and the placement of lasers.
• Audit & Compliance: Develop, implement, and direct annual, risk-based underwriting audits of distribution partners to ensure alignment with corporate guidelines and industry best practices.
• Profitability Monitoring: Continuously analyze developing market results, loss ratios, and financial reports to proactively identify trends, concentrations of loss, or threats to profit objectives.
• Reinsurance Coordination: Review reinsurance programs annually to identify optimization opportunities and structure new program expansions.
• Stakeholder Alignment: Coordinate risk monitoring and regulatory alignment through structured, periodic reporting with senior executives across internal compliance, actuarial, and risk divisions.

Qualifications

• Education: Bachelor’s Degree strong preferred
• Experience: 5–10+ years of deep expertise strictly within Medical Stop Loss insurance underwriting.
• Profitability Track Record: Proven history of meeting or exceeding medical stop loss profitability targets and successfully managing portfolio loss ratios.
• Negotiation & Influence: Demonstrated ability to negotiate sound, complex financial deals and effectively communicate underwriting assessments with internal executives and external partners.
• Technical Savvy: Highly proficient with standard medical stop loss underwriting platforms and advanced data analysis tools.
• Agility: Ability to grasp new products, alternative risk structures (such as captives or level-funded models), and evolving market regulations quickly.

Travel

• Up to 20-25% travel required for distribution partner audits and broker meetings.

This is a permanent position offering outstanding base salary, annual bonus, PTO, industry best medical and retirement benefits, great work life balance, an amazing team to work with and opportunity for advancement within a professional work environment. This is not a remote position and will require the candidate to be in office 5 days a week working closely with the VP and other leadership. Relocation assistance (is) available for someone who will need to relocate.