Context Elicitation & Conversation Evaluation Specialist

OpenTrain AI, Inc.; United States; Remote; USD 34,000 - 55,000; Part time

Job summary

OpenTrain AI, Inc. is seeking a part-time contractor to review AI conversations across relationships, work, education, and wellbeing, identify missing context, and propose clarifying questions.

You will judge whether the AI had enough information to make a recommendation. This remote role requires at least 20 hours per week, English fluency, and relevant professional experience in psychology, social work, counseling, or qualitative research.

Qualifications

• 3 to 5 years of relevant professional experience.
• Background in psychology, social work, counseling, qualitative research, HCI, communication, conflict resolution, coaching, mediation, student services, organizational consulting or related advisory field.
• Experience may include client assessment, interviewing, counseling, case review, conversation analysis, thematic analysis, qualitative coding, or user research.
• English fluency is required.
• Open to candidates in Argentina, Brazil, Chile, Colombia, Mexico, Peru, Romania, Serbia, Bulgaria, India, the Philippines, South Africa, Nigeria, Kenya, and Egypt.

Responsibilities

• Review conversations between people and AI models to identify missing context and assess whether the AI had enough information to make a useful recommendation.
• Document consistent, high-quality findings while working with research teams.
• Suggest follow‑up questions that clarify a person’s needs, limits, or situation.
• Distinguish information that materially affects a recommendation from non-essential details.
• Review conversations involving interpersonal and real-world decision-making situations.

Skills

Qualitative research

Conversation analysis

User research

Interpersonal communication

English fluency

Research documentation

Education

MSW

Social-work credential

Counseling or therapy license

PhD or PsyD

HCI training

Qualitative research training

Job description

Review AI conversations, identify missing context, and suggest follow-up questions that improve recommendations. This part‑time contractor role requires 20 or more hours per week, English fluency, and relevant professional experience.

Remote

Contract, part‑time

Engagement

Remote

Location

Oct 21, 2026

Posted

Open in 15 countries

India + more

• Argentina
• Brazil
• Bulgaria
• Chile
• Colombia
• Egypt
• India
• Kenya
• Mexico
• Nigeria
• Peru
• Philippines
• Romania
• Serbia
• South Africa

The work

You will review conversations between people and AI models in areas such as relationships, work, education, family, planning, wellbeing, and other everyday decisions. Your feedback will help assess whether an AI had enough context to make a useful recommendation.

You will use qualitative review and structured guidelines to identify important missing information and assess whether additional details could have changed the AI's recommendation.

• Identify context the AI should have gathered before making a recommendation.
• Suggest follow‑up questions that clarify a person's needs, limits, or situation.
• Distinguish information that materially affects a recommendation from descriptive or non‑essential details.
• Review conversations involving interpersonal and real‑world decision‑making situations.
• Document consistent, high‑quality findings while working with research teams.

What it pays and takes

Pay details are not provided for this role. The position is part‑time contract work and requires at least 20 hours per week.

• Relevant professional practice or subject‑matter experience: 3 to 5 years.
• Professional background in psychology, social work, counseling, qualitative research, human‑computer interaction, communication, conflict resolution, coaching, mediation, student services, organizational consulting, or a related advisory field.
• Relevant experience may include client assessment, interviewing, counseling, case review, conversation analysis, thematic analysis, qualitative coding, or user research.
• Ability to gather context, understand individual or organizational needs, and provide informed recommendations.
• Helpful qualifications include an MSW, social‑work credential, counseling or therapy license, PhD or PsyD, or advanced training in HCI, communication, anthropology, sociology, or qualitative research.
• English fluency is required.
• Open to candidates in Argentina, Brazil, Chile, Colombia, Mexico, Peru, Romania, Serbia, Bulgaria, India, the Philippines, South Africa, Nigeria, Kenya, and Egypt.
• Part‑time contractor role requiring 20 or more hours per week.

About AI training work

AI training is the human work behind systems that learn from examples, including reviewing model responses and rating whether they are useful. Conversation evaluators help improve how AI understands context and responds to real‑world situations, making relevant professional judgment valuable in the process.