Freelance Legal 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 Legal Expert, you will pair genuine legal expertise with hands-on GenAI-evaluation experience to design challenging, realistic prompts backed by public source documents such as statutes, regulations, court opinions, contracts, and filed pleadings. 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 legal work with an analytical core. You will produce legal deliverables as the output; what makes the work difficult is applying rules to facts and reconciling conflicting provisions across the provided sources. This engagement does not constitute the practice of law, creates no attorney-client relationship, and involves no client representation or legal advice.

What you'll work on

• Apply your legal expertise to help create and evaluate complex AI prompts and responses.
• Conceptualize and draft realistic, multi-step prompts that mirror real legal assignments and require rule application, cross-referencing, and reconciliation of conflicting provisions across multiple source documents.
• 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 standard legal citation and drafting 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

• JD, LLM, JSD, SJD, MLS, or JM from an accredited institution.
• 5+ years of experience in legal writing, litigation, or regulatory compliance.
• Demonstrated ability to read primary source documents (statutes, regulations, court opinions, contracts, filed pleadings) and apply them to factual scenarios across multi-document sets.
• Familiar with statutory interpretation, contractual construction, deadline and limitations computation, and resolution of conflicting provisions.
• 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 legal topics, making outputs more accurate, reliable, and better aligned with real-world legal reasoning.