Claims Manager - AI Evaluator | Remote

Crossing Hurdles; United States; On-site; USD 137,760 - 172,200; Part time

Job summary

Crossing Hurdles is seeking experienced insurance professionals for a remote freelance role focused on evaluating AI-generated claims responses. With a commitment of 15-20+ hours per week, you will assess the accuracy of claims scenarios, provide feedback for model improvement, and address complexities in claims handling. Ideal candidates have 5+ years in claims management and strong analytical skills. Compensation ranges from $100-125/hr, with flexible scheduling and a focus on feedback quality.

Qualifications

• 5+ years of experience in insurance claims, preferably in a managerial role.
• Strong knowledge of claims lifecycle and industry standards.
• Ability to provide structured feedback on AI outputs.

Responsibilities

• Review AI-generated insurance claims responses for accuracy.
• Identify errors and gaps in claims workflows.
• Collaborate with AI development teams asynchronously.

Skills

Insurance claims management

Analytical skills

Written communication

Education

Credentials such as CPCU, ARM, AIC, or SCLA

Job description

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)

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.