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 environment

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 quick, 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)

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