Remote General Counsel — Tech Transactions & AI Contracts

YO AI Labs; Chicago (IL); Remote; USD 110,000 - 193,000; Part time

Job summary

YO AI Labs seeks an experienced General Counsel for a part-time contractor role supporting an innovative legal AI project. The candidate should have strong experience in technology transactions, contract drafting, review, negotiation, and redlining.

You will evaluate AI outputs on contract language, run simulated negotiations, and provide expert feedback to improve AI systems’ ability to identify risks and interpret complex terms. Collaboration with product and research teams is essential.

Qualifications

• 3+ years of in-house legal experience focused on technology transactions.
• Strong hands-on experience with contract drafting, contract review, negotiation, and redlining.
• Experience negotiating MSAs, NDAs, DPAs and other technology agreements.
• Strong analytical and legal reasoning skills.
• Excellent written and verbal communication skills.
• Exceptional attention to detail and ability to translate legal expertise into actionable feedback.

Responsibilities

• Perform simulated contract negotiations, reviews, and redlining exercises.
• Draft and review contracts, including MSAs, NDAs, DPAs, and technology agreements.
• Evaluate AI-generated contract scenarios for accuracy, legal reasoning, and risk identification.
• Provide detailed and actionable feedback to improve AI model performance.
• Develop evaluation frameworks, rubrics, and grading criteria for contract-related AI tasks.
• Identify contractual risks, inconsistencies, and areas requiring revision.
• Collaborate with product and research teams to improve legal AI workflows and guidelines.
• Document legal analysis and recommendations clearly and consistently.

Skills

Contract drafting

Contract review

Negotiation

Redlining

Analytical reasoning

Written communication

Verbal communication

Attention to detail

Cross-functional collaboration

Law- tech AI interest

Job description

YO AI Labs seeks an experienced General Counsel for a part-time contractor role supporting an innovative legal AI project. The candidate should have strong experience in technology transactions, contract drafting, review, negotiation, and redlining.

You will evaluate AI outputs on contract language, run simulated negotiations, and provide expert feedback to improve AI systems’ ability to identify risks and interpret complex terms. Collaboration with product and research teams is essential.