About the Role

Crossing 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 Do Review and assess AI-generated outputs related to claims handling, coverage decisions, and operational workflows Identify errors, gaps, or misalignments in AI reasoning against real-world insurance standards Provide expert written feedback to help train and refine AI models Evaluate scenarios involving claims investigation, documentation, reserving,



and resolution Flag compliance or procedural issues based on your professional experience Domain Focus Property and casualty claims operations Liability and subrogation processes Claims documentation and reserving Coverage interpretation and policy analysis Regulatory compliance in claims handling What We Are Looking For 5 or more years of experience in insurance claims or operations Background in roles such as Claims Manager, Claims Analyst, Insurance Operations Analyst, Subrogation Specialist, or similar CPCU, ARM, ACAS, or FCAS designation is a strong plus Solid understanding of claims lifecycle, coverage analysis, and industry best practices Strong written communication skills and ability to give structured, clear feedback Comfortable working independently in a remote, asynchronous workplace Work Style and Expectations

This 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. Compensation

Rate : $100-125/hr (USD) Payment : Via Deel, fortnightly Commitment : 15-20+ hours/week (minimum 10+ hours/week)

📌 Acturial Analyst | Remote (Winnipeg)
🏢 Crossing Hurdles
📍 Winnipeg