AI Conversation Context Evaluation Specialist

You will evaluate conversations between people and AI models in everyday and interpersonal situations. Your feedback will help assess whether an AI recommendation considered enough context before offering guidance.

You will use structured evaluation guidelines and work carefully with research teams to support consistent assessments.

• Review conversations involving interpersonal and everyday decision-making scenarios.
• Identify missing context and recommend useful follow-up questions.
• Assess whether additional information could have changed an AI recommendation.
• Separate information that materially affects a recommendation from descriptive or non-essential details.
• Record qualitative findings using structured evaluation guidelines.

What It Pays And Takes

This is a remote project expected to last about three weeks. Tasks take approximately 75 minutes on average, and the project requires 20 or more hours per week.

• Pay: Paid per task.
• Project length: Approximately three weeks.
• Time requirement: 20+ hours per week.
• Location: Open to candidates based in Latin America, Southeastern Europe, Asia, or Africa.
• Language: Fluency in English.
• Experience: 3 to 5 years of relevant professional or research experience.
• Relevant backgrounds: Psychology, social work, counseling, therapy, HCI, communication, qualitative research, conflict resolution, coaching, mediation, student services, organizational consulting, or a related advisory field.
• Useful experience: Client assessment, case review, interviewing, counseling, user research, conversation analysis, thematic analysis, qualitative coding, or structured advisory work.
• Credentials that may be relevant: An MSW, applicable social work license, counseling or therapy license, psychology doctorate, or advanced HCI or qualitative research qualification.
• You should be able to draw out context from incomplete information and assess individual or organizational needs before recommendations are made.

How It Works

Apply on OpenTrain with your resume, then complete the application on the hiring site.

About AI Training Work

AI training is the human work behind systems that learn from examples, including reviewing text and rating AI responses. People with experience in research, counseling, communication, or other specialist fields help evaluate whether model outputs are accurate, useful, and appropriately informed.