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.

Interested? Please email your resume to Jason Keck at jkeck@quesstpro.com