Complex Claims & Coverage Director

1 day, 3 hours ago
Weekday

Weekday

Weekday helps companies hire engineers who are vouched by other software engineers, enabling passive income for engineers. They offer services like drafting outreach messages, shortlisting candidates, and conducting reference checks. Backed by Y Combin...

Construction & Engineering
11-50
Founded 2020

Description

  • Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds and carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlements.
  • Create complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations.
  • Write senior-level “golden” reference responses for model training.
  • Grade AI-generated responses using rubrics covering policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline.
  • Identify inconsistent, unsupported, operationally unrealistic, or unauthorized claim-handling positions.
  • Provide written feedback to help the research team improve model behavior.
  • Participate in onboarding office hours and calibration sessions.

Requirements

  • 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims.
  • Experience evaluating coverage issues and developing strategies involving multiple parties, layers, policies, or jurisdictions.
  • Knowledge of insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to counsel.
  • Ability to distinguish operational coverage positions from formal legal advice and identify when legal review is required.
  • Exceptional written reasoning, defensible judgment, and attention to detail.
  • Ability to review incomplete records and separate facts, assumptions, open issues, and recommended next steps.
  • CPCU, AIC, SCLA, ARM, or comparable insurance designation preferred.
  • Experience with complex lines such as excess casualty, professional liability, D&O, cyber, environmental, or construction defect preferred.
  • Experience managing mediations, trials, coverage disputes, extra-contractual exposure, TPAs, adjusters, experts, or panel counsel preferred.
  • Availability for at least 20 hours per week, ideally 40+; immediate start preferred.

Benefits

  • Compensation of $80 per hour.
  • Flexible part-time engagement with a minimum of 20 hours per week.
  • Immediate start with rolling application review.
  • Reasonable accommodations available upon request.

Interested in this position?

Apply directly on the company website

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