Sales Subject Matter Expert (AI Training & Conversation Evaluation)

About This Role

This role involves supporting AI model training and evaluation throughout the sales lifecycle, ensuring AI-generated sales conversations are persuasive, psychologically sound, and human-like. The ideal candidate will have deep sales expertise combined with practical exposure to AI-driven sales systems.

Responsibilities

• Evaluate AI models across prospecting, lead qualification, objection handling, negotiation, and closing stages
• Identify hallucinations, weak persuasion logic, poor objection recovery, and unnatural tone in AI outputs
• Validate AI conversations against real-world sales psychology and conversion principles
• Define evaluation metrics for empathy, deal progression, conversation quality, and persona alignment
• Support data annotation and structured conversation tagging
• Contribute to prompt frameworks adaptable across industries and buyer personas
• Stay current with SPIN, Challenger, Sandler, and modern CRM-driven selling

Requirements

• 7+ years of B2B sales experience
• Strong understanding of pipeline management and multi-stage deal cycles
• Hands-on experience with AI/LLM systems, including reviewing AI-generated conversations, prompt engineering, conversation scoring/evaluation, training data refinement, and rubric creation
• Ability to analyze transcripts and identify why deals succeed or fail
• Exceptional written and verbal communication skills

Qualifications

• 7+ years in B2B sales (Account Executive, Sales Leader, Sales Enablement, etc.)

Nice to Have

• Deep understanding of persuasion psychology
• Data-driven but instinctively aware of human conversation nuance
• Comfortable critiquing AI outputs objectively
• Excited about building AI-powered sales intelligence systems

Skills

* Required skills