Complex Claims & Coverage Director

Role Overview

Help improve advanced AI systems by applying senior-level insurance claims judgment to complex, high-severity, and coverage-sensitive matters. You will develop realistic claims scenarios, assess model responses, and provide expert feedback on disputed coverage, litigation strategy, allocation, and major-loss resolution.

Key Responsibilities

• Design scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds or carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy.
• Create complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations.
• Write senior-quality reference responses for complex technical claims work.
• Evaluate AI-generated responses using structured criteria for policy analysis, strategic judgment, factual support, stakeholder awareness, and appropriate escalation.
• Identify positions that are inconsistent, unsupported by the record, operationally unrealistic, or beyond the authority of a non-lawyer claims professional.
• Provide written feedback used to improve model performance and participate in onboarding office hours and calibration sessions.

Qualifications

• At least 2 years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims.
• Experience evaluating coverage issues and developing claim strategies involving multiple parties, layers, policies, or jurisdictions.
• Understanding of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel.
• Ability to distinguish operational coverage positions from formal legal advice and recognize when specialized legal review is needed.
• Exceptional written reasoning, defensible judgment, and strong attention to detail.
• Comfort reviewing incomplete records and clearly separating facts, assumptions, open issues, and recommended next steps.
• A law degree or license to practice law is not required.

Preferred Qualifications

• CPCU, AIC, SCLA, ARM, or a comparable insurance designation.
• Experience in excess casualty, professional liability, directors and officers, cyber, environmental, construction-defect, or other complex lines.
• Experience managing mediations, trials, coverage disputes, or extra-contractual exposure.
• Home-office technical claims, claim-governance, TPA, independent adjuster, expert, or panel-counsel oversight experience.

Work Terms

• Remote, open to candidates in the United States, Canada, or the United Kingdom.
• Hourly engagement with a minimum commitment of 20 hours per week, ideally 40 or more hours per week.
• The role is available immediately, and applications are reviewed on a rolling basis.
• Successful completion of an estimated 10-hour onboarding process is required before beginning hourly work.

Compensation

• A flat $800 is paid upon successful completion of onboarding.
• After onboarding is completed successfully, compensation is $80 per hour.