Remote AI Conversation Evaluator & Context Specialist

Crossing Hurdles; Italy; Remote; EUR 34,000 - 44,000; Part time

Job summary

Crossing Hurdles is seeking a Text Situated Alignment Specialist for a remote contractor assignment. This 3-week engagement requires 40 hours per week at $32/hour, with full-time weekly commitment rhythm adapted to a short-term project.

You will review AI conversations, identify missing context, and propose precise follow-up questions. Strong background in psychology, counseling, or qualitative research is expected, with experience in interview-style assessments and structured case reviews.

Qualifications

• 3+ years of experience in psychology, social work, counseling, qualitative research, HCI, communication, conflict resolution, coaching, student services, organizational consulting, or related advisory fields.
• Hands-on experience with client assessment, interviewing, counseling, case review, qualitative research, user research, conversation analysis, or similar work.
• Experience identifying relevant context and determining which information is important for informed recommendations.
• Experience with qualitative coding, structured case review, or reviewing client interactions is preferred.

Responsibilities

• Review AI conversations involving real-world interpersonal and everyday decision-making scenarios.
• Identify missing context and recommend relevant follow-up questions.
• Evaluate whether additional information could have changed the AI s recommendations.
• Distinguish between critical, decision-relevant information and non-essential details.
• Conduct qualitative reviews and document findings using structured evaluation guidelines.

Skills

Qualitative research

Interviewing

Conversation analysis

Client assessment

Conflict resolution

Job description

Crossing Hurdles is seeking a Text Situated Alignment Specialist for a remote contractor assignment. This 3-week engagement requires 40 hours per week at $32/hour, with full-time weekly commitment rhythm adapted to a short-term project.

You will review AI conversations, identify missing context, and propose precise follow-up questions. Strong background in psychology, counseling, or qualitative research is expected, with experience in interview-style assessments and structured case reviews.