Complex Claims & Coverage Director

Job summary

Design complex insurance claim scenarios and evaluate AI model outputs against senior technical standards. Provide expert feedback to improve AI reasoning regarding coverage, litigation strategy, and major-loss resolution.

Job details

This role is for one of our clients Compensation: $80 per hour We are partnering with a leading AI lab to train frontier models on high-quality insurance reasoning data. We're hiring Complex Claims and Coverage Directors to design high-severity and coverage-sensitive claim scenarios, evaluate model outputs against established senior claims standards, and help shape how the next generation of AI reasons about disputed coverage, litigation strategy, allocation, and major-loss resolution. We welcome senior carrier claims professionals, complex-claims leaders, coverage specialists, and technical claim directors. This is an insurance-practitioner role and does not require a law degree or license to practice law. What You'll Do Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds, multiple carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy Create work products such as complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations Write "golden" reference responses at senior technical claims quality Grade AI-generated responses against structured rubrics for policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline Identify claim-handling positions that are internally inconsistent, unsupported by the record, operationally unrealistic, or outside the authority of a non-lawyer claims professional Provide written feedback the research team uses to improve model behavior Participate in onboarding office hours and calibration sessions You're a Good Fit If You Have 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims Have evaluated coverage issues and developed claim strategies involving multiple parties, layers, policies, or jurisdictions Understand insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel Can distinguish an operational coverage position from formal legal advice and recognize when specialized legal review is required Demonstrate exceptional written reasoning, defensible judgment, and high attention to detail Are comfortable reviewing incomplete records and clearly separating facts, assumptions, open issues, and recommended next steps Bonus Qualifications CPCU, AIC, SCLA, ARM, or 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 Role Highlights Minimum 20 hours per week (ideally 40+) Role starts immediately, applications reviewed on a rolling basis We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.

What you’ll do

Design complex insurance claim scenarios and evaluate AI model outputs against senior technical standards. Provide expert feedback to improve AI reasoning regarding coverage, litigation strategy, and major-loss resolution.

Requirements

Requires at least 2 years of professional experience handling complex, litigated, or coverage-sensitive insurance claims. Candidates must demonstrate exceptional written reasoning and the ability to distinguish operational coverage positions from legal advice.

Listed skills

• Technical · Preferred
• Settlement · Preferred
• analysis · Preferred
• Organization · Preferred
• Attention to detail · Preferred
• management · Preferred
• discipline · Preferred
• Onboarding · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• Claims handling
• Coverage analysis
• Litigation management
• Settlement strategy
• Policy analysis
• Risk assessment
• Technical writing
• Strategic judgment
• Dispute resolution
• Insurance reasoning
• High-severity claims
• Reservation of rights
• Allocation
• Bad-faith risk management
• Data evaluation
• Litigation Management
• Research
• Artificial Intelligence
• Lawsuits
• Governance
• Litigation Strategy
• Mediation
• Policy Analysis
• Reservations
• Professional Liability
• Detail Oriented

Job areas

• Legal
• Finance & Accounting
• Technology
• Consulting
• Data & Analytics
• Complex Claims Director
• Insurance Lawyer
• Lawyers

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