Sales Subject Matter Expert (AI Training)

Position: Sales Subject Matter Expert (AI Training) | Location: Remote C2C/W2/1099

About the role

We are seeking an experienced Sales Subject Matter Expert (SME) to join our multidisciplinary team supporting the development, evaluation, and improvement of AI models used across the sales lifecycle. The ideal candidate will bridge deep sales expertise and data-driven insights to ensure our AI systems are persuasive, empathetic, context-aware, and aligned with proven sales methodologies and business objectives.

Responsibilities

• Collaborate with AI and Data Teams: Work closely with data scientists and product managers to evaluate AI models used in prospecting, lead qualification, objection handling, negotiation, and closing.
• Model Evaluation & Improvement: Identify gaps, hallucinations, unnatural phrasing, and ineffective tactics in existing models and contribute domain insights to improve conversation quality and conversion potential.
• Validation: Validate AI outputs against real-world sales scenarios, psychological persuasion principles, and customer experience standards to ensure interactions feel human and authentic.
• Define Success Metrics: Define key metrics and success criteria to measure model performance regarding tone, empathy, objection recovery, and eventual deal progression.
• Data Annotation & Context: Support data labeling and annotation by providing specific context on sales stages (e.g., differentiating between a discovery question and a closing question) to refine training datasets.
• Framework Design: Assist in designing prompts and frameworks that allow the AI to adapt to different buyer personas and industries while maintaining consistency.
• Industry Trends: Stay current with evolving sales methodologies (e.g., SPIN, Challenger, Sandler), CRM technologies, and ethical standards in automated selling.

Qualifications

• Education: Bachelor's degree in Business Administration, Marketing, Communications, Psychology, or a related field.
• Experience: 7 years of core sales experience (B2B Account Executive, Inside Sales, Sales Enablement, or Sales Leadership).
• Domain Knowledge: Strong understanding of the full sales funnel, pipeline management, CRM logic, and various sales techniques/methodologies.
• Analytical Mindset: Ability to objectively analyze conversation transcripts and identify why a pitch failed or succeeded.
• Collaboration: Experience collaborating with cross-functional teams (Engineering, Product, Marketing) is highly preferred.