Senior Enterprise Account Executive (AI Training)

Gramian Consultancy is a boutique consultancy specializing in IT professional services and engineering talent solutions. With a strong background in software engineering and leadership, we help companies build high-performing teams by matching them with professionals who truly fit their needs. Role Overview We are looking for experienced B2B and enterprise sales professionals to support the training and evaluation of advanced AI systems. The role focuses on creating and reviewing realistic sales scenarios that test AI capabilities across enterprise prospecting, discovery, qualification, stakeholder management, negotiation, forecasting, and deal closure . The ideal candidate brings substantial quota-carrying experience, a strong track record of closing complex enterprise deals, and deep knowledge of structured sales methodologies and strategic account management. CONTRACT: Short-term contractor assignment, up to 9 weeks COMMITMENT: At least 4 hours per day and up to 40 hours per week, including 4 hours of PST overlap LOCATIONS: Remote from Canada, Brazil, Chile, Mexico, or Colombia PROCESS: 60min Online Test (MCQ, short tasks) Key Responsibilities

• Create expert-level B2B sales tasks and reference solutions based on realistic enterprise scenarios.
• Develop scenarios covering prospecting, discovery, qualification, solution positioning, and deal strategy.
• Evaluate account plans, opportunity strategies, negotiation approaches, and commercial recommendations.
• Review scenarios involving complex multi-stakeholder buying groups , including executives, technical teams, procurement, legal, and finance.
• Assess pipeline quality, forecasting assumptions, deal risks, and next-step strategies.
• Apply formal sales methodologies and established evaluation rubrics to project work.
• Review feedback from senior evaluators and refine outputs accordingly.
• Maintain consistent quality, realism, and commercial accuracy across assigned tasks.
• Contribute to calibration and quality-review cycles.

Requirements

• 8–15 years of quota-carrying B2B or enterprise sales experience .
• Proven track record of meeting or exceeding revenue targets and closing high-value, complex deals.
• Experience managing strategic accounts and long, multi-stakeholder sales cycles.
• Strong command of MEDDIC/MEDDPICC, Challenger, SPIN , or a comparable formal sales methodology.
• Strong expertise in account planning, opportunity qualification, competitive positioning, and deal strategy.
• Advanced experience with commercial negotiation, pipeline management, and forecasting.