Remote Enterprise Sales Coach for AI Training Systems

Confidential; United States; Remote; USD 120,000 - 160,000; Full time

Job summary

Confidential is seeking experienced Enterprise Sales Managers, Regional Sales Managers, and Frontline Sales Leaders to provide coaching, pipeline management, deal strategy, and revenue forecasting guidance. This is a remote contract role focused on evaluating opportunities and training AI models with no quota or direct customer engagement.

Ideal candidates will have recent first-line sales management experience in large organizations, deep B2B sales know-how, and the ability to coach Account

Qualifications

• Recent experience in a first-line sales management role within the past 12 months.
• Experience in organisations with 500+ employees and a sales team of more than 25.
• Strong understanding of B2B sales processes, pipeline management, deal qualification, forecasting, and coaching.
• Ability to evaluate complex opportunities and provide actionable guidance to Account Executives.
• Excellent written communication and analytical skills.
• Must not be employed by GTM/sales tech vendors currently.
• Willingness to complete all assignments independently, without AI tools.

Responsibilities

• Deal Inspection & Qualification: Review enterprise opportunities and assess deal health.
• Sales Coaching & Development: Provide feedback on discovery, stakeholder engagement, and negotiation.
• Pipeline Management & Forecasting: Analyze pipeline and forecast accuracy.
• Strategic Deal Reviews: Evaluate complex B2B scenarios and relationships.
• Performance Assessment: Analyze AE performance and coaching opportunities.
• AI Model Training & Evaluation: Produce analyses to train sales-focused AI models.

Skills

First-line sales management

B2B sales processes

Pipeline management

Forecasting

Sales coaching

MEDDPICC/MEDDIC

Challenger framework

Executive engagement

Tools

MEDDPICC/MEDDIC

Challenger approach

Job description

Confidential is seeking experienced Enterprise Sales Managers, Regional Sales Managers, and Frontline Sales Leaders to provide coaching, pipeline management, deal strategy, and revenue forecasting guidance. This is a remote contract role focused on evaluating opportunities and training AI models with no quota or direct customer engagement.

Ideal candidates will have recent first-line sales management experience in large organizations, deep B2B sales know-how, and the ability to coach Account