Claims Manager - AI Evaluator | Remote

Claims Manager - AI Evaluation Consultant (Remote, Freelance)

Crossing Hurdles is hiring on behalf of a US-based AI frontier lab

About the Role

Our client is building next-generation AI systems and needs experienced insurance professionals to help evaluate and improve how their models reason through complex claims scenarios. This is a remote, freelance engagement designed for senior practitioners who want to apply their domain expertise in a flexible, high-impact capacity.

What You Will Do

• Review and assess AI-generated responses to insurance claims scenarios for accuracy, logic, and practical soundness
• Identify errors, gaps, or hallucinations in how the model handles claims workflows, coverage interpretation, and decision-making
• Provide structured written feedback to help improve model outputs
• Flag edge cases, jurisdiction-specific nuances, and industry-standard deviations
• Collaborate asynchronously with the company's AI development team

Domain Focus

• Property and casualty claims handling
• Coverage analysis and liability determination
• Claims investigation and documentation standards
• Regulatory compliance within claims workflows
• Subrogation, reserving, and settlement processes

What We're Looking For

• 5+ years of experience in insurance claims, with at least some time in a managerial or senior individual contributor capacity
• Target backgrounds: Claims Manager, Senior Claims Analyst, Claims Supervisor, or equivalent Credentials such as CPCU, ARM, AIC, or SCLA are a strong plus
• Solid working knowledge of claims lifecycle, coverage disputes, and multi-line claims handling Strong written communication skills and the ability to give precise, reasoned feedback
• Comfortable working independently in an async environment

Work Style and Expectations

This is a remote freelance role with flexible scheduling. You set your own hours within a weekly commitment range. Work is delivered asynchronously, and you will not be required to attend recurring meetings. The company prioritizes quality of feedback over rigid availability.

Compensation

Rate: $100-125/hr (USD)

Payment: Via Deel, fortnightly

Commitment: 15-20+ hours/week (minimum 10+ hours/week)

Type: Long-term engagement, retainer opportunities for strong performers

You May Be a Good Fit If

You are a senior claims professional who wants to contribute to AI development without leaving your area of expertise. If you have strong opinions about how claims should be handled and can articulate them clearly in writing, this role was built for people like you. To apply, send your resume to Crossing Hurdles for review. Qualified candidates will be contacted for a short onboarding call within 24 hours.