Enterprise Legal AI Evaluation Expert

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. It helps specialists discover opportunities, build a credible profile, and apply to projects that match their expertise. Creating an OpenTrain account is free.

As an OpenTrain contractor, you will contribute specialized legal knowledge to the development and evaluation of advanced AI systems while building experience in a fast-growing technology field.

About AI Training Work

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

This role focuses on document-based generation and evaluation. Your legal judgment will help distinguish rigorous enterprise analysis from responses that are incomplete, superficial, or poorly reasoned.

The Role

OpenTrain is seeking an Enterprise Legal AI Evaluation Expert to create evaluation tasks for AI systems operating in Fortune 500 legal contexts. You will translate complex enterprise legal judgment into realistic scenarios, model-quality reference work, and detailed criterion-referenced rubrics.

The work covers compliance, transactions, risk, reporting, and investigations across large public companies and regulated industries. This is a US-based contractor opportunity requiring 20+ hours per week, with work performed in English.

• Contractor and part-time engagement
• United States applicants
• 20+ hours per week
• English-language work
• $110-$150 per hour

What You'll Do

You will construct legal evaluation scenarios involving in-house counsel, regulatory matters, transactional work, and litigation. You will draft and review materials grounded in major enterprise legal and compliance frameworks, then define the standards used to assess AI-generated work.

Assignments may include contract analysis, risk management, board reporting, and investigations. The goal is to capture the judgment expected from senior counsel working in complex Fortune 500 environments.

• Create realistic scenarios involving in-house counsel, regulatory, transactional, and litigation work.
• Develop materials grounded in FCPA, SOX, GDPR, HIPAA, and sector-specific rules.
• Build tasks around MSAs, SOWs, DPAs, licensing arrangements, and M&A diligence.
• Design ERM- and COSO-aligned risk scenarios and board-level reporting exercises.
• Create regulated-industry investigation scenarios for banking, healthcare, pharmaceuticals, and insurance.
• Write reference answers and criterion-referenced rubrics for complex enterprise legal tasks.
• Evaluate AI responses for legal reasoning, accuracy, completeness, and judgment.

Requirements

This role requires substantial enterprise legal experience and the ability to produce clear legal analysis, reference answers, and evaluation criteria for sophisticated scenarios. You should meet one of the specified experience paths and have deep expertise in at least one relevant enterprise practice area.

• JD with active bar admission.
• At least two years as in-house counsel at a Fortune 500 or large public company, or comparable experience at an AmLaw 100 firm representing Fortune 500 clients.
• Deep expertise in an enterprise practice area such as M&A, securities, regulatory, employment, IP, privacy, or commercial contracting.
• Ability to design realistic legal scenarios and criterion-referenced evaluation rubrics.
• Ability to produce clear legal analysis and high-quality reference answers.
• Familiarity with enterprise compliance regimes.
• Familiarity with CLM or GRC tooling.

Helpful Background

Experience authoring rubrics, examinations, or training content can support the evaluation-design work. Familiarity with enterprise legal and risk systems may also be useful for contract- and compliance-focused workflows.

• Rubric, examination, or training-content authoring
• Ironclad
• Agiloft
• Icertis
• Enterprise GRC tooling

Why Work With OpenTrain

OpenTrain gives AI-training specialists a place to develop a durable professional profile and showcase credible project experience. By contributing legal expertise to AI evaluation, you can help shape how cutting-edge systems reason about complex work while growing in an emerging field.

AI training can provide remote, flexible opportunities for people with specialized knowledge. Your enterprise legal background puts you at the intersection of professional judgment and the technology used to build the next generation of AI.

How to Apply

Create a free OpenTrain account, build your profile around your enterprise legal experience, and apply for this opportunity through OpenTrain. Highlight your practice-area expertise, active bar admission, and experience creating legal analysis or evaluation criteria.