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Weekday, Inc.

Complex Claims & Coverage Director

Posted One Month Ago
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Remote
Hiring Remotely in Canada
Junior
Remote
Hiring Remotely in Canada
Junior
Design complex insurance claim and coverage scenarios for AI model training, including disputed coverage, litigation, allocation, bad-faith risk, and major-loss settlement strategy. Produce senior-level claim analyses, authority requests, reserve rationales, and litigation plans; evaluate AI responses against claims standards; identify unsupported or improper positions; and provide written feedback. Participate in onboarding and calibration sessions.
The summary above was generated by AI

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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