This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Multiline Claims Examiner based in Canada.

This is a unique opportunity for an experienced claims professional to help shape how next-generation AI systems understand and reason about insurance claims. You will bring real-world expertise to the evaluation of AI-generated work across coverage, investigation, damage assessment, negotiation, settlement, and recovery. The role combines hands-on insurance knowledge with structured analysis and professional judgment. You’ll create realistic claims scenarios and benchmark AI responses against the standards expected from experienced claims professionals. Your feedback will directly contribute to improving the quality, accuracy, and reliability of advanced AI models. The engagement is fully remote and designed to provide meaningful work with a defined, short-term commitment.

• Design realistic, domain-specific claims scenarios covering the full claim lifecycle, including first notice of loss, coverage verification, investigation, documentation, reserving, damage evaluation, negotiation, settlement, subrogation, salvage, and closure.
• Develop high-quality professional work products, such as claim action plans, coverage analyses, investigation requests, evaluation summaries, settlement recommendations, and communications with insured parties.
• Produce reference-quality responses that reflect the judgment, methodology, and communication standards expected from experienced claims professionals.
• Review and evaluate five AI-generated responses to each assigned task, ranking them from 1–5 without ties and assigning scores from 0–100.
• Assess AI outputs for factual accuracy, appropriate policy application, sound claims-handling judgment, procedural completeness, and overall quality.
• Identify issues such as premature conclusions, incomplete investigations, unsupported valuations, inappropriate communications, and failures to distinguish covered damage from excluded or unrelated losses.
• Provide clear, evidence-based written rationales that reference specific elements of each response and explain the reasoning behind your evaluation.
• Participate in onboarding sessions, office hours, and calibration activities to ensure consistent and high-quality evaluations.
• Provide structured feedback on the tasks and study design to help improve future evaluation processes.

• 2+ years of professional experience in P&C claims handling, adjusting, or claims examination.
• Demonstrated experience independently managing claims in at least one area such as property, auto physical damage, bodily injury, general liability, commercial casualty, catastrophe, or specialty claims.
• Strong understanding of the complete claims lifecycle, from intake and investigation through evaluation, resolution, recovery, and closure.
• Ability to interpret and apply policy language to specific claim facts while recognizing situations that require escalation or additional investigation.
• Strong analytical judgment and the ability to distinguish routine claim adjudication from complex coverage, litigation, regulatory, or actuarial matters.
• Excellent written communication skills, with the ability to produce clear, specific, evidence-based explanations for professional judgments.
• High attention to detail and the ability to identify subtle errors, omissions, unsupported assumptions, and inconsistencies.
• Current or recent hands-on claims experience, enabling you to assess work from the perspective of a practicing insurance professional.
• Ability to work reliably within a short turnaround window and complete the required evaluation activities independently.
• An insurance designation such as AIC, CPCU, SCLA, or a comparable credential is a plus.
• Multiline or multistate claims experience is advantageous, as is exposure to catastrophe claims, represented bodily injury, litigation, subrogation, SIU, or large-loss claims.
• Experience supervising independent adjusters, experts, vendors, or defense counsel is an additional advantage.
• An active or previously held adjuster license is considered a plus.

• Fully remote engagement that can be completed on your own schedule.
• Short, clearly defined evaluation pilot with an estimated commitment of 8–12 hours.
• Minimum availability of 20 hours per week, with 40+ hours preferred where applicable.
• Opportunity to contribute directly to the development and evaluation of next-generation AI systems using your professional expertise.
• Flexible independent-contractor arrangement with projects that may be extended, shortened, or concluded early depending on project needs and performance.
• Weekly payments through Stripe or Wise, based on services rendered.
• Work that does not require access to confidential or proprietary information belonging to an employer, client, or institution.
• Opportunity to collaborate with researchers and contribute to improving AI capabilities in the insurance domain.
• Referral opportunity offering up to $250 per successful referral, subject to applicable restrictions.
• Applications are reviewed on a rolling basis, with the role starting immediately.
• Please note that H-1B and STEM OPT candidates cannot currently be supported for this engagement.