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Freelance Technical Writing Expert AI Evaluator

Uber AI Solutions is Uber’s marketplace connecting freelancers with Generative AI researchers. We’re inviting experienced technical writing professionals to collaborate on tasks at the frontier of GenAI. This is a freelance, paid opportunity—remote and designed for independent contractors who want to apply their technical writing expertise to help shape how AI handles complex instructional, documentation, and procedural language.

What you’ll work on

  • Apply your technical writing expertise to define ground truth and refine LLM performance.
  • Draft, review, and refine complex, multi-constraint prompts to ensure they are logically sound, precisely structured, and optimized for high-level AI reasoning.
  • Compose "golden responses" that serve as the authoritative target for AI performance, requiring exceptional reasoning, factual precision, and structural clarity.
  • Analyze model-generated responses against established quality guidelines to measure alignment with target expectations.
  • Identify logical fallacies, subtle nuances, and edge cases to ensure every response meets a supreme professional standard.

Engagement details

  • Location: Remote (United States).
  • Type: Freelance / Independent Contractor (1099).

What we’re looking for

  • BA/BS or MA/MS in Technical Communication, English, Computer Science, or a related technical field from an accredited institution.
  • 3+ years of experience in API documentation, software manual authoring, or technical specifications.
  • Prior data annotation or prompt writing experience (strongly preferred).

Ideal backgrounds

  • Technical writers and documentation engineers.
  • UX writers and instructional designers.
  • API and developer documentation specialists.
  • Technical editors and content strategists.

Why this matters: Your expertise will guide how AI systems handle the weight of technical language. By evaluating and refining technical writing prompts and responses, you’ll help ensure that AI is not only accurate but also clear, safe, and procedurally sound for real-world application.