Complex Claims & Coverage Director in Canada Creek, Nova Scotia at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Complex Claims & Coverage Director based in Canada.

This is an opportunity for an experienced insurance professional to help shape how next-generation AI systems reason about complex claims and coverage decisions. You will apply senior-level expertise to realistic scenarios involving disputed coverage, litigation, multiple policies, allocation, and high-severity losses. The role combines deep claims knowledge with structured evaluation and analytical judgment. You will create reference-quality work and assess AI-generated responses against the standards expected of experienced technical claims professionals. Your insights and feedback will directly help improve the accuracy, consistency, and practical judgment of advanced AI models. This is a flexible, fully remote engagement designed for professionals who can bring real-world expertise to a focused evaluation project.

• 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.

• 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.

• 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.