Enterprise Sales Manager – AI Training Specialist

What You'll Do6

• Review enterprise opportunities, assess deal health with methods such as MEDDPICC, flag risks, and recommend ways to advance deals.
• Write structured coaching feedback for Account Executives on discovery, stakeholder engagement, executive alignment, negotiation, and sales execution.
• Analyze pipeline snapshots, forecast categories, and opportunity quality, then identify areas that need management attention.
• Assess complex B2B deals using deal histories, call notes, stakeholder relationships, and execution challenges.
• Evaluate individual Account Executive performance, identify coaching needs, and recommend practical ways to improve sales effectiveness.
• Prepare detailed written analyses and coaching recommendations based on real sales leadership practices for training and evaluating sales-focused AI models.

Requirements7

• Within the past 12 months, have worked in a first-line sales management role directly managing quota-carrying Account Executives.
• Have held that role at an organization with more than 500 employees and a sales team of more than 25 representatives.
• Understand B2B sales processes, pipeline management, deal qualification, forecasting, and sales coaching.
• Be able to assess complex sales opportunities and give Account Executives actionable guidance.
• Have strong written communication and analytical skills, including the ability to explain sophisticated sales strategies with clarity.
• Do not currently work for a company that sells GTM or sales technology, including CRM add-ons, sales engagement platforms, conversation intelligence, or sales data solutions.
• Complete all project assignments without using AI tools.

Preferred Qualifications6

• Prior success as a quota-carrying Account Executive before moving into sales management.
• Experience leading enterprise or mid-market teams that sell B2B software.
• A record of improving team performance, sales productivity, pipeline quality, and forecast accuracy.
• Familiarity with MEDDPICC, MEDDIC, Challenger, or comparable sales frameworks.
• Experience coaching Account Executives on complex, multi-stakeholder enterprise deals with extended sales cycles.
• Knowledge of executive engagement, competitive positioning, and enterprise negotiation strategies.

Who Should Apply

The strongest fit is a current or recent first-line sales leader who has managed quota-carrying Account Executives at a large organization and can assess complex B2B deals. Applicants must be able to complete the work without AI tools and must not work for a sales technology vendor.

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