Technical Documentation AI Evaluation Expert

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. It helps people discover projects, build a professional profile, and apply for opportunities in a fast-growing field where human expertise directly shapes how AI systems work.

About AI Training Work

AI training depends on people who can create examples, assess model behavior, and define what high-quality outputs look like. In this role, your technical writing and editorial judgment will help evaluate how reliably AI agents handle complex documentation and communication tasks.

• Work remotely with flexible, part-time scheduling
• Contribute to cutting-edge AI evaluation and data-labeling work
• Use your professional expertise to shape clearer, more reliable AI behavior

The Role

OpenTrain AI is hiring a Technical Documentation AI Evaluation Expert to create and assess difficult tasks that improve the reliability and usefulness of frontier AI agents. You will work across documentation platforms, developer portals, style guides, release notes, email, repository READMEs, and cross-functional communications.

You will apply editorial and content-governance judgment to produce gold-standard evaluation materials. The role requires 20 or more hours per week and is available worldwide as a part-time contractor position.

• Work type: Part-time contractor
• Time commitment: 20+ hours per week
• Location: Worldwide and fully remote
• Working language: English

What You'll Do

You will author high-difficulty tasks and gold-standard solutions covering technical documentation, style-guide enforcement, content strategy, and structural editing. Each task should include enough context and evaluation guidance to distinguish exceptional, acceptable, and deficient work.

You will review, calibrate, and critique work against rigorous editorial and technical quality standards. You will use raw technical inputs and simulated documentation environments to verify technical accuracy, feasibility, and practical realism.

You will also assess the editorial reasoning behind final artifacts, identify edge cases and rubric ambiguities, and incorporate feedback through calibration and revision cycles.

• Create difficult AI evaluation tasks and editing scenarios
• Define task context, reference materials, expected deliverables, and scoring rubrics
• Evaluate accuracy, voice, tone, organization, terminology consistency, and accessibility
• Review technical documentation for feasibility, realism, and editorial quality
• Identify ambiguous requirements and edge cases in evaluation rubrics
• Revise and calibrate materials based on structured feedback

Required Experience and Skills

You should have 8 to 15 years of hands-on experience in technical writing, editorial strategy, content architecture, or documentation engineering. A bachelor's degree or equivalent practical experience is required.

Experience creating or maintaining enterprise style guides and content-governance frameworks is required. You should also be comfortable translating highly technical subjects into clear, structured, and accessible content while evaluating the accuracy, voice, tone, structure, terminology, accessibility, and editorial rationale of documentation.

• 8-15 years of relevant technical writing, editorial strategy, content architecture, or documentation engineering experience
• Experience creating or maintaining enterprise style guides and content-governance frameworks
• Strong knowledge of editorial standards, single-sourcing, and documentation systems
• Practical knowledge of Markdown, Docs-as-Code, DITA, Notion, or Confluence
• Ability to create challenging AI evaluation tasks, editing scenarios, and gold-standard rubrics
• Ability to evaluate technical content for accuracy, structure, terminology consistency, accessibility, voice, and tone

Relevant Documentation Work

Your experience may include producing or reviewing a range of technical and editorial deliverables. The role is suited to professionals who can combine strong writing judgment with structured evaluation and content-governance expertise.

• Enterprise style guides and content-governance frameworks
• API documentation or technical specifications
• Architecture overviews and developer guides
• Migration plans and documentation-system content
• Comprehensive editorial reviews
• Single-sourced or Docs-as-Code documentation

Helpful Background

Experience with AI evaluation, data annotation, content review, quality assurance, complex editing scenarios, or evaluation rubrics is helpful. These skills can support the careful creation and review of materials used to measure AI performance.

• AI evaluation or data annotation
• Content review and quality assurance
• Complex editing scenarios
• Evaluation rubric design and calibration

Build Your AI Training Career

OpenTrain gives contributors one place to discover AI training opportunities, build a profile, and grow a lasting portfolio. Creating an OpenTrain account is free, and your experience can help you find projects aligned with your technical documentation and editorial expertise.

• Create a free OpenTrain account
• Showcase credible technical writing and evaluation experience
• Discover remote opportunities across the AI training industry
• Build a portfolio around specialized AI evaluation work