Complex Claims & Coverage Director at Weekday 1

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.

Requirements

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.

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