Remote Junior Transactional Attorney: AI Contracting

YO AI Labs; Chicago (IL); Remote; USD 90,000 - 120,000; Full time

Job summary

YO AI Labs is seeking a Junior Transactional Attorney to support a legal AI project involving contract drafting, review, redlining, and negotiation. The role focuses on evaluating AI-generated contract work and offering legal feedback to improve accuracy, consistency, and risk identification.

As a contractor, you will collaborate with the legal, product, and research teams to apply structured evaluation criteria and provide actionable guidance, while working in a remote setting.

Qualifications

• 1–3 years of transactional legal experience in-house or at a law firm.
• Experience with MSAs, NDAs, and other commercial agreements.
• Strong contract drafting, review, and redlining skills.
• Excellent written communication and analytical abilities.
• Strong attention to detail and understanding of contractual risk.
• Interest in legal technology and AI applications.
• Experience with LPAs, ISDAs, M&A, or fund formation is a plus.

Responsibilities

• Perform contract drafting, review, redlining, and negotiation exercises.
• Review AI-generated responses to transactional legal scenarios.
• Evaluate contract language for accuracy, risk, and consistency.
• Apply structured evaluation criteria to assess AI performance.
• Provide clear and actionable legal feedback.
• Collaborate with legal, product, and research teams.

Skills

Contract Redlining

Contract Negotiation

Contract Drafting

MSAs

NDAs

LPAs

ISDAs

Legal Research

Contract Review

Risk Assessment

Written Communication

Legal Analysis

Job description

YO AI Labs is seeking a Junior Transactional Attorney to support a legal AI project involving contract drafting, review, redlining, and negotiation. The role focuses on evaluating AI-generated contract work and offering legal feedback to improve accuracy, consistency, and risk identification.

As a contractor, you will collaborate with the legal, product, and research teams to apply structured evaluation criteria and provide actionable guidance, while working in a remote setting.