Workspace Personalization AI Evaluator

Use your business experience to help improve personalized AI

OpenTrain AI is looking for a Workspace Personalization AI Evaluator to test how effectively AI assistants support real business tasks across Google Workspace.

This role is aimed specifically at U.S.-based business owners who manage teams of more than 10 people and use Gmail, Drive, Calendar, Chat, Docs, Sheets, Slides, and Meet as part of their daily operations.

You’ll create realistic workplace scenarios, interact with AI chatbots, and assess whether their answers make appropriate use of available business context. The work is less about technical AI knowledge and more about applying practical judgment: Is the response accurate? Did it understand the request? Is the personalization useful, or did the system make assumptions it shouldn’t have?

The work

You’ll test AI assistants using prompts based on common small-business needs and evaluate the quality of the resulting conversations.

Typical tasks include:

• Writing realistic business prompts around scheduling, communication, documents, files, and team operations.
• Holding short, multi-turn conversations with different AI chatbots.
• Reviewing answers for accuracy, relevance, clarity, completeness, and appropriate personalization.
• Spotting missing details, incorrect context retrieval, and irrelevant recommendations.
• Comparing model responses and explaining which one performs better.
• Submitting conversation transcripts and structured evaluation feedback.
• Following detailed project instructions while protecting confidential information.

Who this role is for

This project has unusually specific eligibility requirements. Applicants must:

• Live in the United States.
• Own or run a business with more than 10 employees.
• Have substantial experience managing small-business operations.
• Use Gmail as their main business email platform.
• Be highly familiar with Google Workspace, particularly Google Chat, Drive, and Calendar.
• Feel comfortable testing AI tools and chatbot experiences.
• Have strong analytical and critical-thinking skills.
• Be able to provide clear, objective written feedback.
• Work independently and follow structured evaluation guidelines.

Previous professional experience in AI evaluation is not required.

Why your perspective matters

Personalized AI assistants are expected to understand far more than an isolated prompt. They may need to interpret previous emails, calendar events, documents, files, and workplace activity without misusing that information.

By testing these systems with authentic business scenarios, you’ll help identify where they understand context correctly, where they overlook important details, and where personalization becomes inaccurate or unhelpful.

What the role offers

• Fully remote contractor work.
• Flexible part-time availability.
• A minimum commitment of 20 hours per week.
• Entry-level access to AI training and evaluation projects.
• Practical experience working with generative AI and RLHF-style evaluation.
• An opportunity to apply real business knowledge to the development of workplace AI products.