Enterprise Account Executive - AI Sales Expert

Confidential; United States; Remote; USD 96,000 - 193,000; Full time

Job summary

Confidential is seeking experienced Enterprise and Strategic Account Executives for a 100% remote contract role in the United States. The role focuses on complex B2B sales, account strategy, and enterprise deal execution without quotas or direct customer interactions.

You will develop strategic analyses to train AI models, map stakeholders, and craft executive-level messaging for sales leadership. Independence and strong written communication are essential.

Qualifications

• Recent experience in a quota-carrying Enterprise, Strategic, or Mid-Market/Enterprise Account Executive role within the past 12 months.
• Experience at an organization with 500+ employees and a sales team >25 representatives.
• Strong understanding of enterprise sales processes, deal qualification, stakeholder management, and complex B2B cycles.
• Excellent written communication and ability to articulate sophisticated sales strategies clearly.
• Must not currently be employed by a company selling GTM or sales tech.
• Willingness to complete all project assignments independently, without AI tools.

Responsibilities

• Account Research & Discovery: Analyse prospective accounts, identify business challenges, formulate strategic discovery questions.
• Deal Qualification & Strategy: Evaluate opportunities using MEDDPICC, assess deal health, and propose next steps.
• Stakeholder Mapping: Identify key decision-makers within complex enterprise buying committees.
• Executive Engagement: Prepare strategic briefs for executive conversations with value propositions.
• Objection Handling & Negotiation: Assess objections and negotiation scenarios to suggest approaches.
• AI Model Training & Evaluation: Produce high-quality written analyses to train enterprise selling AI models.

Skills

Quota-carrying AE

Large org experience

Enterprise sales process

Written communication

Independent work

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 and Strategic Account Executives to contribute their expertise in complex B2B sales, account strategy, and enterprise deal execution.

In this role, you will apply your real-world sales experience to evaluate realistic enterprise sales scenarios and develop high-quality analyses that help train and improve AI systems. This is not a traditional sales position. There are no quotas, prospecting requirements, or direct customer interactions. Instead, you will use your professional judgment to demonstrate how top-performing Account Executives approach complex sales situations.

Key Responsibilities

• Account Research & Discovery: Analyse prospective accounts, identify business challenges, develop pain hypotheses, and formulate strategic discovery questions.

• Deal Qualification & Strategy: Evaluate sales opportunities using established methodologies such as MEDDPICC, assess deal health, and recommend actionable next steps.

• Stakeholder Mapping: Identify key decision-makers, economic buyers, champions, and influencers within complex enterprise buying committees.

• Executive Engagement: Develop strategic briefs for executive-level conversations, including meeting preparation, value propositions, and stakeholder-specific messaging.

• Objection Handling & Negotiation: Assess realistic sales objections, competitive positioning, and negotiation scenarios to recommend effective approaches.

• AI Model Training & Evaluation: Produce structured, high-quality written analyses that reflect expert-level enterprise selling practices and support the development of sales-specialised AI models.

Required Qualifications

• Recent experience in a quota-carrying Enterprise, Strategic, or Mid-Market/Enterprise Account Executive role within the past 12 months.

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

• Strong understanding of enterprise sales processes, deal qualification, stakeholder management, and complex B2B sales cycles.

• Excellent written communication skills and 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

• 5+ years of quota-carrying B2B sales experience, preferably in enterprise or strategic accounts.

• Demonstrated history of consistently meeting or exceeding sales quotas, including President's Club recognition or comparable achievements.

• Experience managing complex, multi-stakeholder enterprise deals involving extended sales cycles.

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

• Strong experience engaging senior executives, navigating procurement processes, and developing account strategies.

Why Join This Project?

• Shape the Future of AI: Apply your enterprise sales expertise to help develop AI systems that understand sophisticated B2B selling.

• Leverage Your Experience: Contribute strategic insights without the pressure of quotas, prospecting, or managing an active sales pipeline.

• Competitive Compensation: Earn premium hourly rates for your specialised industry knowledge.

• 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.