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OpenTrain AIFor AI Companies

Enterprise GTM AI Evaluation Expert

Use Fortune 500 sales, marketing, or RevOps expertise to create realistic AI evaluation tasks, reference outputs, and rubrics for enterprise go-to-market decisions. Remote contract work pays $60-$70 per hour.

OpenTrain AI

Generative AI & RLHF

100% Remote Hourly · $60–$70/hr

$60–$70/hr

Compensation

Worldwide

Eligibility

Entry

Experience

Aug 7, 2026

Posted

Open worldwide

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About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. OpenTrain AI is hiring and contracting for this opportunity, giving specialists a way to apply their professional judgment to the development of advanced AI systems.

Creating an OpenTrain account is free. You can build a profile that reflects your experience, discover relevant AI training projects, and apply in minutes.

About AI Evaluation Work

AI training is the human side of building artificial intelligence. Specialists create examples, write scenarios, review model responses, and develop evaluation criteria that help AI systems produce more accurate and useful results.

In this role, your enterprise go-to-market experience will help distinguish credible sales, marketing, and RevOps judgment from generic playbook recall. Your work will shape how AI systems reason about complex business decisions.

The Role

OpenTrain is seeking an Enterprise GTM AI Evaluation Expert to create evaluation tasks for AI systems operating in Fortune 500 go-to-market contexts. The work focuses on $1M+ annual contract value deals, complex stakeholder groups, procurement demands, and the brand stakes of large public companies.

You will translate authentic senior sales, marketing, and RevOps judgment into realistic scenarios, reference outputs, and evaluation rubrics. The role is remote and structured as a contract position, with part-time work available.

  • Remote contractor opportunity
  • Default commitment of 40 hours per week
  • Minimum listed time requirement of 20+ hours per week
  • Pay of $60-$70 per hour
  • English-language work
  • Part-time contract engagement

What You'll Do

You will design text-based generation and evaluation tasks that reflect the realities of enterprise go-to-market work. Your scenarios and reference materials should capture the budgets, stakeholders, processes, and judgment required in large-company environments.

  • Construct enterprise sales scenarios involving $1M+ ACV deals, multi-stakeholder buying committees, and complex procurement cycles at Fortune 500 accounts.
  • Build marketing tasks covering Fortune 500 brand strategy, enterprise account-based marketing, scaled demand generation, lifecycle programs, and category positioning.
  • Develop RevOps and go-to-market scenarios involving Salesforce Enterprise, Marketo, 6sense, Gong, and Outreach workflows.
  • Apply MEDDIC, Challenger, and Force Management approaches when producing reference deal strategies, account plans, and executive narratives.
  • Author rubrics that assess whether an AI system demonstrates credible enterprise go-to-market judgment.

Required Experience And Skills

This role requires at least five years of experience selling, marketing, or leading RevOps at a Fortune 500 enterprise software vendor or within a Fortune 500 brand or marketing organization. The structured listing identifies the opportunity as entry level, but the role-specific requirements call for substantial enterprise experience.

You should be able to reason about enterprise buying committees, budgets, procurement, legal review, stakeholder complexity, executive communication, account strategy, and large-enterprise buying processes.

  • At least five years of relevant Fortune 500 enterprise sales, marketing, or RevOps experience.
  • Direct ownership of Fortune 500 accounts, brand campaigns, or demand programs.
  • Fluency with enterprise go-to-market tools and methodologies.
  • Ability to reason about budgets, procurement, and legal review.
  • Strong judgment about stakeholder complexity, executive communication, account strategy, and enterprise buying processes.

Helpful Background

Prior experience authoring evaluation rubrics, sales-enablement curricula, or training content is helpful. Familiarity with the tools and methodologies below can support the scenario-building work.

  • Salesforce
  • Marketo
  • 6sense
  • Gong
  • Outreach
  • MEDDIC
  • Challenger
  • Force Management

Why Work With OpenTrain

AI training and data labeling are among the fastest-growing ways to work in tech. People with specialized professional knowledge can help build the examples and evaluations behind modern AI systems while working remotely with flexible schedules.

OpenTrain helps you manage AI training opportunities, present credible experience in one profile, and build a longer-term portfolio in the field. Apply through OpenTrain to bring your enterprise go-to-market expertise to cutting-edge AI evaluation work.

  • Work remotely with a computer or phone and an internet connection.
  • Use specialized enterprise expertise in a growing AI industry.
  • Build a profile and portfolio around AI training experience.
  • Apply in minutes with a free OpenTrain account.

Ready to apply?

Create a free OpenTrain account and apply for this role in minutes.

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