Complex Claims and Coverage Director for AI Model Training

Role Overview

Shape frontier AI systems by applying senior-level insurance claims judgment to complex, high-severity, and coverage-sensitive matters. You will create realistic claim scenarios, assess AI-generated work against established claims standards, and help improve reasoning related to coverage disputes, litigation strategy, allocation, and major-loss resolution.

Key Responsibilities

• Develop realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds and 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.
• Produce senior-quality reference responses for complex technical claims work.
• Evaluate AI-generated responses using structured rubrics covering policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline.
• Identify positions that are inconsistent, unsupported by the record, operationally unrealistic, or beyond the authority of a non-lawyer claims professional.
• Provide written feedback to support improvements in model behavior.
• 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.
• Knowledge of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel.
• Ability to distinguish an operational coverage position 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 while 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 with 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 or claim-governance experience.
• Experience overseeing TPAs, independent adjusters, experts, or panel counsel.

Work Terms

• Remote role open to candidates in the United States, Canada, or the United Kingdom.
• Per-task engagement.
• Minimum commitment of 20 hours per week, with 40 or more hours preferred.
• Immediate start, with applications reviewed on a rolling basis.

Compensation

• $800 per task.

Application Process

Submit an application for rolling review. Selected candidates can begin immediately and will participate in onboarding and calibration activities.