Enterprise Sales Expert - F500 Specialist - AI Trainer

Role Responsibilities

• Construct enterprise sales scenarios spanning $1M+ ACV deals, multi-stakeholder buying committees, and complex procurement cycles at F500 accounts.
• Build marketing tasks across F500 brand strategy, enterprise ABM, demand generation at scale, lifecycle, and category positioning.
• Develop RevOps and GTM scenarios involving Salesforce Enterprise, Marketo, 6sense, Gong, and Outreach in F500 stacks.
• Apply enterprise sales methodologies (MEDDIC, Challenger, Force Management) and produce reference deal strategies, account plans, and executive narratives.
• Author rubrics that distinguish authentic enterprise GTM judgment from generic playbook recall.

Qualifications

• Must-Have:
  • 5+ years selling, marketing, or running RevOps at a Fortune 500 enterprise software vendor or inside an F500 brand or marketing organization.
  • Direct ownership of F500 accounts, F500 brand campaigns, or F500 demand programs.
  • Fluency in enterprise GTM tooling and methodologies, plus understanding of how F500 budgets, procurement, and legal review actually work.
• PREFERRED:
  • Prior rubric, sales-enablement curriculum, or training-content authorship.

Compensation & Legal

• Hourly contractor, paid weekly via Stripe Connect.

Application Process

Upload resume
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Support/Resources

• Interview process/platform details
• Support

Job Details

Location: Chicago, Remote, United States
Job Type: remote
Posted: May 31, 2026
Categories: Marketing, Data Annotation, Sales

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