Claims Manager - AI Evaluator | Remote

About the role

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

Responsibilities

• 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

Requirements

• 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

Qualifications

• Senior claims professional who wants to contribute to AI development without leaving their area of expertise
• Strong opinions about how claims should be handled and can articulate them clearly in writing

Skills

• Domain expertise in 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

Pay

Compensation Rate: $100-125/hr (USD)

Schedule

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.

Benefits

• The company prioritizes quality of feedback over rigid availability.

Benefits

To apply, send your resume to Crossing Hurdles for review. Qualified candidates will be contacted for a short onboarding call within 24 hours.