Claims Operations Specialist - Remote Freelance AI EvaluationAbout the RoleCrossing Hurdles is partnering with a leading US-based AI frontier lab to source experienced insurance professionals for a remote freelance engagement. The company is building out a specialized team of domain experts to evaluate and improve AI systems used in insurance operations. This is a paid, flexible, long‐term opportunity designed for working professionals who want to contribute to AI development without leaving their field.What You Will DoReview and assess AI-generated outputs related to claims handling, coverage decisions, and operational workflowsIdentify errors, gaps, or misalignments in AI reasoning against real-world insurance standardsProvide expert written feedback to help train and refine AI modelsEvaluate scenarios involving claims investigation, documentation, reserving, and resolutionFlag compliance or procedural issues based on your professional experienceDomain FocusProperty and casualty claims operationsLiability and subrogation processesClaims documentation and reservingCoverage interpretation and policy analysisRegulatory compliance in claims handlingWhat We Are Looking For5 or more years of experience in insurance claims or operationsBackground in roles such as Claims Manager, Claims Analyst,



Insurance Operations Analyst, Subrogation Specialist, or similarCPCU, ARM, ACAS, or FCAS designation is a strong plusSolid understanding of claims lifecycle, coverage analysis, and industry best practicesStrong written communication skills and ability to give structured, clear feedbackComfortable working independently in a remote, asynchronous environmentWork Style and ExpectationsThis is a remote, self‐managed engagement. You will complete evaluation tasks on your own schedule within agreed weekly hour targets. No meetings‐heavy workflow. Onboarding is fast, typically within 24 hours of acceptance. The company values quality of feedback over volume, so attention to detail and professional rigor matter here.CompensationRate$100-125/hr (USD)PaymentVia Deel, fortnightlyCommitment15-20+ hours/week (minimum 10+ hours/week)You May Be a Valuable Fit IfYou are an experienced claims professional looking to apply your expertise in a new way, want flexible remote work that fits around existing commitments, are curious about AI and how it is being developed for insurance use cases, and want to be paid competitively for your domain knowledge without taking on a full-time role change.

📌 Claims Operations Specialist | Remote (Ottawa)
🏢 Crossing Hurdles
📍 Ottawa