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About AI Training Work AI training is the human side of building artificial intelligence. Contributors review and evaluate model outputs so AI systems can become more relevant, accurate, helpful, and reliable in real-world interactions.
This work is remote and can offer flexible part-time schedules. It is a direct way to contribute to cutting-edge AI development while using skills such as careful reasoning, written communication, and attention to detail.
Evaluate model responses and identify quality issues.
Provide structured human feedback that supports better AI behavior.
Work remotely with a computer and internet connection.
The Role OpenTrain is recruiting a Personalized AI Response Evaluator to assess how well AI systems use context from connected applications. You will review personalized responses based on email, calendar, photo, file, and business account activity.
You will judge relevance, accuracy, helpfulness, and appropriate personalization while following evaluation guidelines and confidentiality requirements. The work is designed for an entry-level contractor, and previous AI evaluation or annotation experience is helpful but not required.
Role: Personalized AI Response Evaluator
Engagement: Part-time contractor
Location: Current residence in Canada
Time commitment: 20+ hours per week
Expected duration: Up to 16 weeks
Working language: English




What You'll Do You will evaluate AI-generated responses using personalized prompts and connected application context. Your reviews will help identify whether an AI system retrieves and applies information appropriately.
The work requires nuanced judgment and clear written explanations. You will compare responses, identify subtle problems, and document your reasoning in structured feedback while protecting confidential information.
Assess whether responses are relevant, accurate, helpful, and appropriately personalized.
Identify unsupported assumptions, incorrect personalization, inconsistencies, and irrelevant recommendations.
Compare multiple responses and select the one that provides the stronger user experience.
Write clear, detailed, well-reasoned feedback according to evaluation guidelines.
Review retrieval quality using eligible connected applications and available account context.
Requirements And Helpful Background You should be comfortable analyzing nuanced AI responses and spotting subtle inconsistencies. You must actively use common productivity or consumer applications with sufficient account history for context-based evaluation and be willing to connect eligible applications for personalized prompt evaluation.
A bachelor's degree or equivalent practical experience in any field is expected. Previous experience in AI evaluation, data annotation, content review, quality assurance, or another analytical role is helpful, but it is not required.
Current residence in Canada.
Robust analytical judgment and attention to detail.
Excellent written communication for structured evaluation feedback.
Experience using common productivity or consumer applications with sufficient account history.
Willingness to connect eligible applications for personalized evaluation.
Ability to work independently while following confidentiality requirements.
Reliable computer and internet connection.
Bachelor's degree or equivalent practical experience in any field.

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📌 Personalized AI Response Evaluator (Manitoba)
🏢 OpenTrain AI
📍 Manitoba