Hiring: Director, Stop Loss Underwriting Company: Questpro Location: Cincinnati, OH Job Posted Time: 2026-09-17 11:31:41 Employment Type: Remote About the job Experience: •10+ years of deep expertise strictly within Medical Stop Loss insurance underwriting. Required Skills: •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: •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. •Up to 20-25% travel required for distribution partner audits and broker meetings. •Interested? Please email your resume to Jason Keck at jkeck@quesstpro.com Compensation: •Flexible work environment (work from home / hybrid options) Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!