Freelance Technical Writing 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 Technical Writing Expert, you will pair genuine technical documentation expertise with hands-on GenAI-evaluation experience to design challenging, realistic prompts backed by source documents such as API specifications, technical design documents, data schemas, and functional requirements. 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 documentation work with an analytical core. You will author technical documents as the deliverable; what makes the work difficult is identifying where source specifications are incomplete, inconsistent, or contradictory before you write.

What you'll work on

• Apply your technical writing expertise to help create and evaluate complex AI prompts and responses.
• Conceptualize and draft realistic, multi-step prompts that mirror real documentation assignments and require specification validation, cross-reference tracing, and reconciliation 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 validation.
• Produce fully correct, deliverable-quality golden responses that satisfy all criteria using industry-standard 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

• BA/BS or MA/MS in Technical Communication, English, Computer Science, or a related technical field from an accredited institution.
• 5+ years of experience in API documentation, software manual authoring, or technical specifications, technical writers or documentation engineers, UX writers and instructional designers with specification experience.
• Demonstrated ability to read primary source documents (API specifications, technical design documents, data schemas, functional requirements) and evaluate them for logical completeness and internal consistency.
• Familiar with API specification formats (OpenAPI/Swagger), schema validation, and structured authoring frameworks.
• 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 technical topics, making outputs more accurate, reliable, and better aligned with real-world engineering documentation standards.