Workspace Personalization AI Evaluator

About OpenTrain

OpenTrain AI is the hiring and contracting organization for this role. OpenTrain is the leading platform for finding and building careers in AI training and data labeling, helping people discover projects, build a professional profile, and grow in a fast-moving technology field.

• Free account creation
• Opportunities to build experience in AI training and evaluation
• A direct way to contribute to the development of modern AI systems

About AI Training Work

AI training is the human side of building artificial intelligence. Evaluators review model outputs, test AI systems with realistic prompts, and provide structured feedback so models become more accurate, relevant, and useful.

• Work directly with cutting-edge AI tools
• Use human judgment to assess model quality
• Help shape how AI systems respond to real-world needs

The Role

OpenTrain AI is seeking a Workspace Personalization AI Evaluator to assess AI-generated responses using personalized prompts across Google Workspace applications. You will create business-related scenarios, interact with AI chatbots, and evaluate whether their responses are accurate, relevant, complete, personalized, and useful.

This role focuses on Workspace Personalization Evals and is designed for a US-based business owner with more than 10 employees who has substantial experience with small business operations and Google Workspace.

• Contractor and part-time engagement
• 20+ hours per week
• English-language work
• US-based applicants only
• Entry-level experience designation

What You’ll Do

You will follow structured evaluation guidelines while testing AI chatbot conversations and documenting your findings. Your feedback will support model improvements by identifying where AI responses succeed or fail in realistic business contexts.

• Create realistic business-related prompts based on defined user goals
• Interact with multiple AI chatbots in conversations of up to five turns
• Assess response clarity, usefulness, accuracy, relevance, personalization, and completeness
• Provide structured feedback and comparative evaluations
• Identify incorrect context retrieval, missing information, and irrelevant responses
• Submit conversation transcripts and evaluation results

Requirements

This role requires practical business experience and strong familiarity with Google Workspace. You should be comfortable using AI tools, applying objective judgment, and following detailed evaluation instructions while maintaining confidentiality.

• Business owner with more than 10 employees
• Strong understanding of small business operations
• Strong analytical and critical thinking skills
• Gmail must be your primary business communication tool
• High familiarity with Gmail, Chat, Calendar, Drive, Docs, Sheets, Slides, and Meet
• Heavy usage of Google Chat, Drive, and Calendar
• Comfort interacting with AI tools and chatbots
• Ability to follow structured evaluation guidelines
• Ability to provide clear, objective feedback
• Ability to maintain confidentiality

Why This Work Matters

Every major AI system depends on people who can assess outputs against real-world expectations. By bringing your small-business experience to personalized Workspace evaluations, you will help improve how AI understands context and supports business users.

• Apply real operational judgment to AI evaluation
• Work remotely with flexible part-time potential
• Gain experience in a rapidly growing AI training industry