[Hiring] Complex Claims & Coverage Director @Weekday AI

Role Description

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.
• Help shape how the next generation of AI reasons about disputed coverage, litigation strategy, allocation, and major-loss resolution.

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.

Qualifications

• 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 an operational coverage position from formal legal advice and recognize when specialized legal review is required.
• Exceptional written reasoning, defensible judgment, and high attention to detail.
• Comfort with 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.