Contract Redlining Attorney

OpenTrain AI, Inc.; Northern (KY); Hybrid; USD 117,000 - 145,000; Part time

Job summary

OpenTrain AI, Inc. is seeking a contract redlining attorney to support AI training and evaluation through technology transaction workflows. You will perform simulated contract negotiations and review AI responses to contract scenarios.

You will help create evaluation frameworks and provide actionable feedback to improve model outputs and contract-review processes, collaborating with product and research teams. This remote, part-time role offers competitive hourly compensation.

Qualifications

• At least three years of in-house technology transactions experience.
• Negotiation of MSAs, NDAs, and DPAs.
• Strong drafting, review, negotiation, and redlining capabilities.
• Excellent written and verbal communication with meticulous attention to detail.
• Ability to translate legal expertise into feedback for AI systems.

Responsibilities

• Perform simulated negotiations and redlining for technology contracts.
• Review AI-generated responses to contract scenarios and assess accuracy, risk analysis, and legal judgment.
• Create objective evaluation frameworks and grading criteria for contract-related model performance.
• Provide actionable feedback to improve model outputs and contract-review workflows.
• Help refine data, guidelines, and best practices for AI-driven legal review solutions.
• Collaborate with product and research teams on legal AI evaluation work.

Skills

In-house experience

MSA negotiation

NDA negotiation

DPA negotiation

Contract drafting

Redlining

Written communication

Analytical judgement

Cross-functional

Job description

About OpenTrain

OpenTrain is the centralized, open platform where AI training and data-labeling freelancers find work, consolidate opportunities across platforms, and build a unified AI training portfolio they control. We make specialized AI training work easier to track, apply for, and grow into a durable freelance career.

About this role

OpenTrain is recruiting a contract redlining attorney to support AI training and evaluation through technology transaction workflows. You will perform simulated contract negotiations, review AI responses to contract scenarios, and provide expert feedback that helps models identify legal risk and interpret contract language with greater precision. The role focuses on practical commercial judgment across drafting, review, negotiation, and redlining.

What you will do

Perform simulated negotiations and redlining exercises for technology contracts. Review AI-generated responses to contract scenarios and assess their accuracy, risk analysis, and legal judgment. Create objective evaluation frameworks and grading criteria for contract-related model performance. Provide actionable feedback to improve model outputs and contract-review workflows. Help refine data, guidelines, and best practices for AI-driven legal review solutions. Collaborate with product and research teams on legal AI evaluation work.

Required skills

At least three years of in-house experience focused on technology transactions. Hands‑on experience negotiating master services agreements, nondisclosure agreements, and data processing agreements. Strong contract drafting, review, negotiation, and redlining capabilities. Excellent written and verbal communication with meticulous attention to detail. Strong analytical judgment and the ability to translate legal expertise into clear feedback for AI systems. Experience working with cross-disciplinary teams.

Helpful background

Prior exposure to AI, legal technology, or training initiatives is helpful. Experience at a corporate law firm in mergers and acquisitions or private‑equity fund formation is also relevant.

Schedule, location, and compensation

This is a remote, part-time contractor opportunity. Compensation is $85‑$105 per hour.

Why work with OpenTrain

OpenTrain gives freelancers one place to manage AI training opportunities instead of rebuilding proof of work on every platform. A stronger OpenTrain profile helps you show credible experience, discover roles that match your skills, and turn AI training and data-labeling work into a long‑term portfolio.