Freelance Insurance Claims Expert AI Evaluator

Uber AI Solutions is Uber's marketplace connecting skilled freelancers with Generative AI researchers and product teams working on cutting-edge AI systems. We partner with independent contractors to support large-scale model evaluation, alignment, and quality initiatives.

As a Freelance Insurance Claims Expert, you will pair genuine claims expertise with hands-on GenAI-evaluation experience to design challenging, realistic prompts backed by source documents such as policy forms and endorsements, state insurance regulations, loss run reports, and claims files. You will then probe where the model breaks, and encode expert judgment into precise, gradable rubrics and a canonical 'golden' answer. You own an end-to-end evaluation task from prompt design through reviewer sign-off.

This is hands-on analytical work — applying policy language to claim facts and deriving coverage determinations, not handling live claims. No actual claims are adjudicated, no coverage decisions are issued, and no policyholder data is handled.

What you'll work on

• Apply your claims expertise to help create and evaluate complex AI prompts and responses.
• Conceptualize and draft realistic, multi-step prompts that mirror real claims assignments and require coverage rule application, cross-referencing, and reconciliation of policy language against claim facts.
• Identify and document genuine model failures by writing specific, objective, and actionable explanations.
• Build comprehensive evaluation rubrics that trace each required input through dependent criteria and carefully separate extraction from determination.
• Produce fully correct, deliverable-quality golden responses that satisfy all criteria using industry-standard claims documentation conventions.
• Complete our onboarding process and strictly follow the disciplined authoring and review workflow for each task.
• Closely follow guidelines, run AI quality checks on your own work, and resolve any issues in the feedback loop before final submission.

Engagement details

• Location: Remote (United States)
• Engagement Type: 1099 Freelance / Independent Contractor, through the Uber AI Solutions platform
• Engagement Duration: 40 hours over 1-2 weeks

Who we're looking for

• 7+ years of professional experience as a licensed Claims Adjuster.
• CPCU (Chartered Property Casualty Underwriter). CCP, FCLA, or PTC also valued.
• Experience with multi-line claims (property, liability, specialty) or complex coverage disputes, possibly an active state Claims Adjuster license.
• Demonstrated ability to interpret policy forms and endorsements, apply coverage rules to factual claim scenarios, and determine the extent of insurer liability.
• Demonstrated ability to read primary source documents (policy forms, state insurance regulations, loss run reports, claims files) and derive multi-step coverage determinations from them.
• Comfortable working independently on detail-oriented tasks.
• Strong analytical and written communication skills.
• Prior hands-on experience with GenAI / LLM evaluation and prompt engineering, rubric or golden-answer authoring, data annotation, RLHF, red-teaming, or model quality assessment.

Why this matters

Your expertise will help improve how AI systems handle complex insurance topics, making outputs more accurate, reliable, and better aligned with real-world claims reasoning.