Enterprise Insurance AI Evaluation Expert

About OpenTrain

OpenTrain AI is the hiring and contracting organization for this role and the #1 platform for finding and building careers in AI training and data labeling. We help specialists discover meaningful AI projects, build a professional profile, and apply in minutes.

This contract gives experienced insurance professionals an opportunity to turn industry judgment into structured evaluation work that helps improve advanced AI systems.

• Contractor and part-time engagement
• Remote and open worldwide
• Apply and manage your AI training profile through OpenTrain

About AI Training and Evaluation Work

AI training is the human side of building artificial intelligence. Expert contributors create scenarios, write reference answers, and assess model outputs so AI systems can handle complex professional decisions with greater accuracy and consistency.

In this role, your insurance knowledge will help distinguish authentic professional judgment from generic textbook responses or licensing-exam recall. The work combines domain expertise, structured analysis, and clear written communication.

• Help shape how advanced AI systems understand insurance decisions
• Create realistic examples and evaluation standards
• Work remotely with flexible part-time scheduling

The Role

OpenTrain is seeking an Enterprise Insurance AI Evaluation Expert to create evaluation tasks for AI systems operating in complex commercial insurance and enterprise risk contexts. You will translate senior insurance judgment into realistic scenarios, reference outputs, and scoring rubrics that reflect underwriting complexity, regulatory stakes, and claims scale.

The project is listed as entry level, while the role itself requires at least five years of relevant insurance, actuarial, claims, or risk management experience. The expected commitment is 20 or more hours per week, with compensation of $50 to $60 per hour.

• Pay: $50-$60 per hour
• Time requirement: 20+ hours per week
• Work arrangement: Remote, worldwide
• Engagement type: Contractor and part time
• Primary language: English

What You’ll Do

You will design insurance evaluation tasks that test practical decision-making across commercial operations, enterprise risk, and regulatory environments. Your work will include scenarios, reference outputs, and rubrics that clearly separate strong professional reasoning from incomplete or generic answers.

• Construct scenarios covering commercial underwriting, multi-stakeholder claims adjudication, regulatory filings, and compliance review cycles
• Build tasks across underwriting and risk assessment, claims management, actuarial pricing and reserving, reinsurance strategy, and regulatory affairs
• Develop insurance operations scenarios involving Guidewire, Duck Creek, SAS, R, and enterprise claims or policy administration systems
• Apply actuarial risk modeling, loss reserving, enterprise risk management frameworks, and NAIC compliance standards
• Produce reference underwriting guidelines, claims strategies, executive-level risk narratives, and evaluation rubrics
• Design assessments that measure authentic professional judgment rather than textbook or licensing-exam recall

Requirements

This role is intended for an experienced insurance professional who can explain complex decisions clearly through written scenarios, reference answers, and evaluation criteria. Direct ownership of substantial insurance, claims, actuarial, or risk responsibilities is required.

• At least five years of experience in underwriting, claims, actuarial work, or risk management within a major insurance carrier, reinsurer, or enterprise risk organization
• Direct ownership of large-scale underwriting portfolios, claims operations, or actuarial pricing models
• Practical understanding of regulatory compliance, reinsurance treaties, loss reserving, and enterprise insurance decision-making
• Ability to create realistic insurance scenarios, reference outputs, and evaluation rubrics that assess professional judgment
• Familiarity with Guidewire, Duck Creek, SAS, R, or similar policy, claims, or actuarial platforms
• Experience authoring evaluation rubrics, actuarial or underwriting training curricula, or claims documentation is helpful

Who Should Apply

Apply if you have worked directly with complex insurance decisions and can turn that experience into precise, understandable evaluation content. This may be a strong fit for professionals from major carriers, reinsurers, or enterprise risk organizations with experience spanning underwriting, claims, actuarial pricing, reserving, reinsurance, or compliance.

You should be comfortable explaining why one insurance response is stronger than another and defining criteria that an AI system can be evaluated against.

• Insurance professionals with substantial commercial or enterprise experience
• Underwriters, claims leaders, actuaries, and risk management specialists
• Professionals familiar with insurance policy, claims, or actuarial systems
• Clear writers who can document nuanced judgment in structured formats

How to Get Started

Create a free OpenTrain account, build a profile that reflects your insurance experience, and apply to this contract in minutes. OpenTrain helps you organize AI training opportunities and build a portfolio that showcases credible specialist work over time.

• Create your free OpenTrain account
• Highlight your insurance, actuarial, claims, and risk experience
• Apply to the Enterprise Insurance AI Evaluation Expert contract
• Use completed AI training work to strengthen your long-term professional portfolio