Contract Redlining Attorney – Legal AI Evaluation

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. We help people discover opportunities, build a professional profile, and grow experience in a rapidly expanding industry where human expertise shapes how advanced AI systems work.

About Legal AI Training

AI training is the human side of building artificial intelligence. Legal professionals contribute by reviewing model responses, evaluating reasoning, identifying risks, and providing feedback that helps AI systems become more accurate, reliable, and useful in specialized fields such as technology contracting.

The Role

OpenTrain is seeking a Contract Redlining Attorney to help train and evaluate legal AI systems through realistic technology-contract workflows. You will apply practical experience in drafting, reviewing, negotiating, and redlining agreements to assess model performance, identify legal risk, interpret contract language, and provide sound legal judgment.

This is a part-time, remote contractor opportunity for an attorney familiar with how MSAs, NDAs, and DPAs are handled in technology transactions. You will translate that experience into clear, actionable guidance for AI systems.

• Employment type: Part-time contractor
• Work arrangement: Remote and worldwide
• Time commitment: 20+ hours per week
• Language: English
• Compensation: $80–$200 per hour

What You'll Do

You will perform legal AI evaluation and feedback work involving contract analysis, simulated negotiations, and redlining exercises. The work requires consistent legal reasoning and careful attention to distinctions in contract language and negotiation outcomes.

• Perform simulated contract negotiations and redlining exercises involving technology agreements.
• Review AI responses to contract scenarios for accuracy, precision, and treatment of legal risk.
• Provide expert feedback to improve model performance and legal contract analysis.
• Develop objective evaluation frameworks and grading criteria for AI performance on contract tasks.
• Collaborate with product and research teams to refine data, guidelines, and practices for AI-driven contract review.
• Identify important distinctions in contract language and negotiation outcomes.
• Explain legal judgment and contractual risk in clear, actionable terms.

Required Qualifications

This role requires a J.D. from an ABA-accredited law school and active admission to at least one U.S. state bar or other U.S. jurisdiction. Candidates should have at least three years of focused experience negotiating or reviewing technology contracts.

• Practical experience with MSAs, NDAs, and DPAs, including contract redlining.
• Ability to identify contractual risk and interpret complex contract language.
• Strong written and verbal communication skills.
• Meticulous attention to detail and rigorous analytical ability.
• Ability to convert legal expertise into practical feedback and consistent evaluation criteria for AI systems.
• Ability to collaborate across legal, product, or research disciplines.

Helpful Background

Prior exposure to artificial intelligence, legal technology, or training initiatives is helpful. Demonstrated interest in applying legal expertise to the development of more capable and reliable AI systems is valuable.

• Experience evaluating AI-generated legal responses.
• Interest in legal AI and emerging technology.
• Experience creating guidelines, rubrics, or structured assessment criteria.

Why Work in AI Training

AI training and data-labeling work offers a way to contribute directly to cutting-edge technology while using the expertise you already have. Remote projects and flexible part-time schedules can make this work compatible with other professional commitments, while a strong project history can support a growing career in AI training.

• Apply specialized legal knowledge to the development of advanced AI systems.
• Work remotely on practical contract-analysis and model-evaluation tasks.
• Use your experience in technology transactions in a growing technical field.
• Build experience in legal AI evaluation and human feedback work.