Enterprise Insurance AI Evaluation Expert

About OpenTrain

OpenTrain AI is the #1 platform for finding and building careers in AI training and data labeling. We help contributors discover meaningful projects, build a professional profile, and apply to opportunities that put their expertise to work shaping modern AI systems.

About AI Training Work

AI training is the human side of building artificial intelligence. Experienced professionals create examples, review model outputs, and define the standards that help AI systems produce more accurate, useful, and domain-aware results.

• Work remotely with flexible, part-time scheduling
• Apply real-world professional judgment to cutting-edge AI development
• Help distinguish authoritative insurance expertise from generic or superficial answers

The Role

OpenTrain AI is seeking an Enterprise Insurance AI Evaluation Expert to build evaluation tasks and reference materials for AI systems used in Fortune 500-scale enterprise insurance operations. You will design realistic scenarios, draft authoritative reference outputs, and create rubrics that capture the depth of real-world insurance judgment.

This is a contractor, part-time opportunity for a senior insurance professional with direct experience in underwriting, claims, actuarial work, or risk management at a large insurance carrier, reinsurer, or enterprise risk organization.

• Work worldwide on a remote basis
• Commit 20+ hours per week
• Earn $50–$60 per hour
• Work as a contractor

What You'll Do

You will create text-based evaluation and generation tasks grounded in authentic enterprise insurance workflows. Your work should reflect how large organizations approach risk, claims, pricing, reserving, reinsurance, regulatory obligations, and executive decision-making.

• Construct scenarios involving complex commercial underwriting, multi-stakeholder claims adjudication, and regulatory filing or compliance review cycles
• Build tasks across underwriting and risk assessment, claims management, actuarial pricing and reserving, reinsurance strategy, and regulatory and compliance affairs
• Develop scenarios involving Guidewire, Duck Creek, actuarial modeling platforms such as SAS and R, and enterprise claims and policy administration systems
• Apply actuarial risk modeling, loss reserving, enterprise risk management frameworks, and NAIC compliance standards
• Produce reference underwriting guidelines, claims strategies, and executive-level risk narratives
• Author rubrics that distinguish authentic enterprise insurance judgment from generic textbook or licensing-exam recall

Required Experience

This specialist role requires substantial experience in large-scale insurance operations. Candidates should be able to explain how enterprise insurance decisions are made in practice, not simply reproduce textbook concepts.

• 5+ years in underwriting, claims, actuarial, or risk management at a Fortune 500 insurance carrier or reinsurer
• Experience at a large enterprise insurance or risk organization, such as a major carrier or reinsurer
• Direct ownership of Fortune 500-scale underwriting portfolios, claims operations, or actuarial pricing models
• Fluency in enterprise insurance tooling and methodologies
• Understanding of Fortune 500 regulatory compliance, reinsurance treaties, and reserving practices
• Ability to author rubrics that distinguish authentic enterprise insurance judgment from textbook recall

Helpful Background

Experience translating professional expertise into clear evaluation criteria will be especially useful in this role.

• Prior authorship of rubrics
• Actuarial or underwriting training curriculum development
• Claims documentation authorship

How This Work Shapes AI

Every major AI system depends on examples and reviews prepared by people with real subject-matter expertise. By creating rigorous insurance scenarios and evaluation standards, you will help AI systems better reflect the judgment used in complex enterprise insurance environments.

• Create an OpenTrain profile for free
• Apply your insurance expertise to specialized AI training work
• Build experience in a fast-growing field at the intersection of professional knowledge and artificial intelligence