AI Conversation Evaluation Specialist | $32/hr Remote

Crossing Hurdles; United States; Remote; USD 36,000 - 52,000; Part time

Job summary

Crossing Hurdles is seeking a Text Situated Alignment Specialist on a remote contractor assignment. The role focuses on reviewing AI conversations to identify missing context, suggest relevant follow-up questions, and assess how information could influence recommendations.

This position emphasizes qualitative coding, structured case reviews, and detailed documentation. The successful candidate will bring 3+ years in advisory fields, hands-on client assessment experience, and a proven ability to

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.

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

Interviews and counseling

Context identification

Conversation analysis

Job description

Position: Text Situated Alignment Specialist

Type: Contractor Assignment

Compensation: $32/hour

Location: Remote

Commitment: Full-time (40 hours/week), for 3 weeks

Role 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.

Requirements

• 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.