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Sales Subject Matter Expert (AI Training & Conversation Evaluation)

Sales Subject Matter Expert (AI Training & Conversation Evaluation)

Remote

United states

Senior

Freelance

13-02-2026

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Skills

Communication Negotiation Sales Persuasion Prospecting Lead Qualification Objection Handling CRM Training

Job Specifications

Location: Remote

Experience: 7+ Years in B2B Sales + AI/LLM Experience Required

Engagement: Contract / Project-Based (Immediate Start)

About the Role

We are seeking a seasoned Sales Subject Matter Expert (SME) to support AI model training and evaluation across the sales lifecycle.

You will ensure AI-generated sales conversations are persuasive, psychologically sound, human-like, and aligned with proven sales methodologies.

This role requires deep sales experience plus practical exposure to AI-driven sales systems.

Key Responsibilities

Evaluate AI models across:
Prospecting
Lead qualification
Objection handling
Negotiation
Closing
Identify:
Hallucinations
Weak persuasion logic
Poor objection recovery
Unnatural tone or phrasing
Validate AI conversations against real-world sales psychology and conversion principles.
Define evaluation metrics for:
Empathy
Deal progression
Conversation quality
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.

Mandatory Requirements

7+ years of B2B sales experience (Account Executive, Sales Leader, Sales Enablement, etc.).
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
Rubric creation
Ability to analyze transcripts and identify why deals succeed or fail.
Exceptional written and verbal communication skills.

Ideal Profile

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

Immediate hiring. Serious candidates with AI + Sales experience only.

Email : sajid.ahmed@truelancer.com