Complex Claims & Coverage Director

Accountabilities:

• • Design realistic, high-complexity claims scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds and carriers, allocation, litigation, mediation, bad-faith risk, and major-loss settlement strategy.
  • Develop professional work products such as complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations.
  • Produce "golden" reference responses that reflect the quality, reasoning, judgment, and communication expected from senior technical claims professionals.
  • Evaluate AI-generated responses using structured criteria covering policy analysis, strategic judgment, factual support, stakeholder awareness, and appropriate escalation.
  • Identify responses that contain internally inconsistent positions, unsupported conclusions, operationally unrealistic recommendations, or actions outside the appropriate authority of a non-lawyer claims professional.
  • Assess whether proposed claims strategies appropriately account for available evidence, policy provisions, stakeholder interests, litigation considerations, and potential financial or extra-contractual exposure.
  • Provide detailed, evidence-based written feedback that research teams can use to improve AI model behavior and reasoning.
  • Participate in onboarding office hours and calibration sessions to maintain consistency and quality throughout the evaluation process.
  • Clearly distinguish established facts from assumptions, unresolved issues, and recommended next steps when working with incomplete or evolving claim records.

  Requirements

  • 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims.
  • Demonstrated experience evaluating coverage issues and developing claim strategies involving multiple parties, insurance layers, policies, or jurisdictions.
  • Strong understanding of insurer duties, reservation-of-rights practices, litigation management, settlement authority, escalation procedures, and collaboration with internal or external counsel.
  • Ability to distinguish an operational coverage position from formal legal advice and recognize when specialized legal review is necessary.
  • Exceptional written reasoning skills, with the ability to explain complex claims judgments clearly, logically, and defensibly.
  • Strong attention to detail and the ability to evaluate incomplete records while clearly separating facts, assumptions, open questions, and recommendations.
  • Sound professional judgment and the ability to identify approaches that are technically unsupported, procedurally inappropriate, or inconsistent with claims-handling standards.
  • An insurance designation such as CPCU, AIC, SCLA, ARM, or a comparable credential is a strong advantage.
  • Experience with complex lines such as excess casualty, professional liability, directors and officers, cyber, environmental, construction defect, or other specialty insurance is beneficial.
  • Experience managing mediations, trials, coverage disputes, or extra-contractual exposure is a plus.
  • Experience with claims governance, home-office technical claims functions, or oversight of TPAs, independent adjusters, experts, or panel counsel is advantageous.
  • A current or previously held adjuster license is an additional asset.

  Benefits

  • Fully remote independent-contractor engagement.
  • Flexible schedule, allowing you to complete the work on your own schedule.
  • Minimum commitment of 20 hours per week, with 40+ hours preferred.
  • Opportunity to contribute directly to the development and evaluation of next-generation AI systems through your insurance expertise.
  • Meaningful project work focused on complex claims, coverage analysis, and senior-level professional judgment.
  • Opportunity to collaborate with leading AI researchers and help improve AI capabilities in the insurance domain.
  • Projects may be extended, shortened, or concluded early depending on project needs and performance.
  • No requirement to access confidential or proprietary information belonging to an employer, client, or institution.
  • Weekly payments through Stripe or Wise, based on services rendered.
  • Role starts immediately, with applications reviewed on a rolling basis.
  • Referral opportunity offering up to $250 per successful referral, subject to applicable restrictions.
  • Please note that H-1B and STEM OPT candidates cannot currently be supported for this engagement.