Complex Claims Director - Insurance - AI Trainer

Obsidian; Chicago (IL); On-site; USD 120,000 - 180,000; Part time

Job summary

Mercor, in collaboration with a leading AI lab, seeks a Complex Claims and Coverage Director to design high-stakes coverage scenarios and evaluate model outputs against senior standards.

You will shape dispute resolution strategies, create comprehensive claim plans, and provide feedback to improve AI reasoning in insurance contexts.

Qualifications

• 2+ years experience handling complex, litigated, high-severity, or coverage-sensitive claims.
• Experience evaluating coverage issues across multiple parties, layers, policies, or jurisdictions.
• Understanding insurer duties, reservation-of-rights practices, litigation management, settlement authority.
• Ability distinguish operational coverage position from formal legal advice; recognize when legal review is needed.
• Exceptional written reasoning, defensible judgment, and high attention to detail.

Responsibilities

• Design realistic scenarios involving disputed coverage, rights reservations, excess exposure, multiple insureds and carriers, allocation, litigation, mediation, 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 gold-standard 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 inconsistent, unsupported, or outside the authority of non-lawyer claims professionals.
• Provide written feedback to the research team to improve model behavior.
• Participate in onboarding office hours and calibration sessions.

Skills

Complex claims handling

Litigation management

Coverage analysis

Technical reasoning

Written communication

Education

CPCU / AIC / SCLA / ARM designation

Job description

About the Role

Mercor is 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