Contract Redlining Attorney — Legal AI Evaluation

About OpenTrain

OpenTrain is the centralized platform where people build careers in AI training and data labeling. We help freelancers find specialized projects, consolidate proof of work, and grow a durable portfolio of AI training experience — creating a single place to manage and showcase this kind of freelance work.

OpenTrain AI is the hiring and contracting organization for this role. Creating an OpenTrain account is free and makes it faster to discover, apply for, and manage AI training projects that match your legal expertise.

About AI training for legal work

AI training (also called data labeling or human feedback) is the human work that teaches models to read, reason, and act. In legal projects, that means helping models recognize contract risk, draft precise redlines, and respond to negotiation scenarios — shaping how AI systems handle real-world legal language.

This work is remote and flexible, often part‑time, and is an opportunity to apply legal skills directly to the development of tools used across the legal and technology industries.

The role

You will serve as a contract redlining attorney focused on legal AI evaluation. The role centers on simulated negotiations, redlining exercises, assessment of AI outputs in contract scenarios, and development of objective grading criteria and evaluation frameworks.

You will collaborate with the OpenTrain team to improve data, annotation guidelines, and best practices so AI systems better identify risk and produce precise, defensible legal language.

What you'll do

• Perform simulated contract negotiations and redlining exercises on MSAs, NDAs, DPAs, and related documents.
• Review and assess AI responses to contract scenarios, judging accuracy, completeness, and legal risk identification.
• Design and document evaluation frameworks, rubrics, and grading criteria for contract-related tasks.
• Collaborate on annotation guidelines, sample annotations, and best-practice notes to improve training data quality.

Requirements

• J.D. from an ABA-accredited law school.
• Active bar admission in at least one U.S. jurisdiction.
• At least 3 years of in-house technology transactions experience.
• Hands-on experience negotiating MSAs, NDAs, and DPAs.
• Ability to redline contracts and judge AI-generated legal outputs with precision.
• Strong written and verbal communication skills and careful attention to legal detail.
• Prior exposure to AI, legal tech, or training initiatives is preferred (but not strictly required).

Schedule, pay, and logistics

This is part-time remote contractor work with flexible scheduling. Estimated commitment is about 20 hours per week over a 1–3 month engagement window.

Pay rate is $80 to $105 per hour (PAY_PER_HOUR, USD). The role is contractor status and work is performed remotely; candidates worldwide may apply but must hold an active U.S. bar admission as required above.

How to apply

Create a free OpenTrain account, complete your profile, and submit your application for this contract role. Your profile helps demonstrate relevant experience and prior work samples.

OpenTrain AI is the contracting organization for this role and will manage onboarding, guidelines, and payment for selected contractors.