Enterprise Sales Manager – AI Training Specialist

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

our partner is partnering with a leading AI company to develop advanced AI models designed to support enterprise sales teams. We are seeking experienced Enterprise Sales Managers, Regional Sales Managers, and Frontline Sales Leaders to contribute their expertise in sales coaching, pipeline management, deal strategy, and revenue forecasting. In this role, you will leverage your sales leadership experience to evaluate realistic B2B sales scenarios, assess deal execution, and develop high-quality coaching recommendations that help train and improve AI systems. This is not a traditional sales management position. You will not be responsible for managing employees, carrying a sales quota, or engaging directly with customers. Instead, you will apply your professional judgment to demonstrate how effective frontline sales leaders evaluate opportunities, coach Account Executives, and drive sales performance.

Key Responsibilities

• Deal Inspection & Qualification: Review enterprise sales opportunities, assess deal health using established methodologies such as MEDDPICC, identify potential risks, and recommend strategies to improve deal progression.

• Sales Coaching & Development: Provide structured, actionable feedback to Account Executives on discovery, stakeholder engagement, executive alignment, negotiation, and overall sales execution.

• Pipeline Management & Forecasting: Analyse pipeline snapshots, evaluate forecast categories, assess opportunity quality, and identify areas requiring management attention.

• Strategic Deal Reviews: Evaluate complex B2B sales scenarios, including deal histories, call notes, stakeholder relationships, and sales execution challenges.

• Performance Assessment: Analyse individual Account Executive performance, identify coaching opportunities, and recommend practical improvements to sales effectiveness.

• AI Model Training & Evaluation: Develop detailed written analyses and coaching recommendations that reflect real-world sales leadership practices and contribute to the training and evaluation of sales-specialised AI models.

Required Qualifications

• Recent experience in a first-line sales management role within the past 12 months, directly managing a team of quota-carrying Account Executives.

• Experience in such a role at an organisation with 500+ employees and a sales team of more than 25 representatives.

• Strong understanding of B2B sales processes, pipeline management, deal qualification, forecasting, and sales coaching.

• Demonstrated ability to evaluate complex sales opportunities and provide actionable guidance to Account Executives.

• Excellent written communication and analytical skills, with the ability to articulate sophisticated sales strategies clearly.

• Must not currently be employed by a company selling go-to-market (GTM) or sales technology, including CRM add-ons, sales engagement platforms, conversation intelligence, or sales data solutions.

• Willingness to complete all project assignments independently, without the use of AI tools.

Preferred Qualifications

• Previous success in a quota-carrying Account Executive role before transitioning into sales management.

• Experience leading enterprise or mid-market sales teams selling B2B software solutions.

• Demonstrated success in improving team performance, sales productivity, pipeline quality, and forecast accuracy.

• Familiarity with structured sales methodologies such as MEDDPICC, MEDDIC, Challenger, or similar frameworks.

• Experience coaching Account Executives through complex, multi-stakeholder enterprise deals involving extended sales cycles.

• Strong understanding of executive engagement, competitive positioning, and enterprise negotiation strategies.

Why Join This Project?

• Shape the Future of AI: Apply your sales leadership expertise to help develop AI systems capable of understanding sophisticated B2B sales management practices.

• Leverage Your Leadership Experience: Contribute your expertise in coaching, forecasting, and deal strategy without the responsibilities of directly managing a sales team.

• Potential for Growth: Access opportunities for increased project involvement as the engagement expands.

This is a 100% remote contract role. Applicants must be located in: United States.