Enterprise Product AI Evaluation Expert

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. OpenTrain AI is recruiting and contracting for this role, giving experienced professionals a way to apply their expertise to cutting-edge AI systems while building a lasting portfolio of training work.

Creating an OpenTrain account is free. This is a remote, part-time contractor opportunity available worldwide.

About AI Evaluation Work

AI training is the human side of building artificial intelligence. Expert contributors create examples, assess model outputs, and establish standards that help AI systems produce more useful and reliable results.

In this role, your enterprise product judgment will help distinguish genuinely strategic product thinking from generic framework recall. You will shape evaluation tasks around the scale, stakeholder complexity, and business stakes of Fortune 500 organizations.

The Role

OpenTrain is seeking an Enterprise Product AI Evaluation Expert to build evaluation tasks for AI systems operating in Fortune 500 enterprise product contexts. You will design realistic product scenarios, draft reference outputs, and write rigorous rubrics that reflect how senior enterprise product leaders think and make decisions.

This is an intermediate-level contractor role requiring at least 20 hours per week. Compensation is $80–$90 per hour, and the working language is English.

• Employment type: Contractor, part-time
• Time commitment: 20+ hours per week
• Compensation: $80–$90 USD per hour
• Location: Worldwide and fully remote
• Working language: English

What You'll Do

You will translate authentic Fortune 500 product experience into high-quality AI evaluation content. Your work will cover product strategy, discovery, research, platform decisions, commercial planning, and product operations.

• Construct enterprise product scenarios involving multi-quarter roadmaps, cross-functional alignment, and complex go-to-market or platform decisions at Fortune 500 scale.
• Build product tasks across product strategy, discovery and user research, pricing and packaging, platform and API product management, and product-led growth.
• Develop product operations scenarios using tools such as Jira, Productboard, Amplitude, Mixpanel, Figma, and enterprise experimentation platforms.
• Apply JTBD, RICE and opportunity scoring, dual-track agile, and OKR methodologies.
• Produce reference PRDs, roadmap strategies, and executive-level product narratives.
• Author rubrics that separate authentic enterprise product judgment from generic framework or bootcamp-level responses.
• Design product evaluation tasks, rubrics, and training content for AI systems.

Required Experience

This role is intended for an experienced product manager or product leader who has directly operated at Fortune 500 scale. You should be able to demonstrate how product decisions connect to measurable business impact and how enterprise governance shapes execution.

• At least 5 years of product management or product leadership experience at a Fortune 500 technology or enterprise organization.
• Direct ownership of Fortune 500-scale products, platforms, or product lines with measurable business impact.
• Fluency in enterprise product tooling, including Jira, Productboard, Amplitude, and Figma.
• Experience with enterprise product methodologies such as JTBD, RICE, and OKRs.
• Understanding of Fortune 500 budgets, cross-functional governance, and executive stakeholder alignment.
• Ability to author rubrics and reference PRDs.
• Experience designing product evaluation tasks, rubrics, or training curricula for AI systems.

Helpful Background

Prior authorship of rubrics, product-training curricula, or PRDs and other product documentation is a plus. Experience may come from a Fortune 500 technology company or from a product organization within a large non-technology enterprise.

• Product leadership experience at organizations such as Google, Amazon, Microsoft, Salesforce, or Adobe.
• Product experience within large enterprises such as JPMorgan, UPS, Unilever, or PepsiCo.
• Background creating structured product guidance, evaluation standards, or training materials.

Build Your AI Training Career

AI training and data labeling are growing fields where specialists help shape how modern AI systems behave. OpenTrain provides a single place to manage projects, build a professional portfolio, and grow your career in this emerging industry while remaining an independent contractor.