Civil litigation Expert - Remote

YO AI Labs; Chicago (IL); Remote; USD 83,000 - 131,000; Part time

Job summary

YO AI Labs is seeking an experienced AI Legal Fellow in Litigation & Motion Practice for a remote, part-time contractor role. The fellow will evaluate and improve AI-generated legal advocacy by reviewing AI-produced work and providing expert feedback on arguments and authorities to refine writing and litigation strategy.

The role emphasizes developing objective evaluation criteria, mentoring AI outputs, and collaborating with research and product teams to advance AI guidelines.

Qualifications

• Substantial civil litigation experience in federal court.
• Strong writing and analytical abilities for legal feedback.
• Ability to evaluate AI-generated legal work and provide actionable guidance.
• Experience working in remote, cross-functional teams is preferred.

Responsibilities

• Draft and evaluate litigation motions, briefs, and strategy exercises.
• Review AI-generated responses to federal litigation scenarios.
• Assess arguments, authorities, facts, organization and persuasive writing.
• Develop objective evaluation criteria and grading frameworks for AI work.
• Provide clear, actionable feedback to improve AI performance.
• Collaborate with research and product teams to refine guidelines and training materials.

Skills

Motion Drafting

Federal Litigation

Civil Procedure

Legal Writing

Research & Analysis

Remote Collaboration

Job description

AI Legal Fellow — Litigation & Motion Practice

Role Type: Contractor
Location: Remote
Engagement: Part-Time, Project-Based

Job Summary

We are seeking experienced Litigators with strong federal civil litigation and motion-practice experience to support a specialized project focused on evaluating and improving AI-generated legal advocacy.

Fellows will review AI-generated legal work, assess the quality of arguments and authorities, and provide expert feedback to improve legal reasoning, writing, and litigation strategy.

Key Responsibilities

• Draft and evaluate litigation motions, briefs, and legal strategy exercises.
• Review AI-generated responses to federal litigation scenarios.
• Assess legal arguments, use of authority, factual analysis, organization, and persuasive writing.
• Develop objective evaluation criteria and grading frameworks for AI-generated legal work.
• Provide clear, actionable feedback to improve AI performance.
• Collaborate with research and product teams to refine legal AI guidelines and training materials.

Required Skills

• Motion Drafting
• Federal Litigation
• Civil Litigation
• Federal Court Experience
• Civil Procedure
• Legal Research & Writing
• Trial & Litigation Strategy
• Critical Thinking
• Attention to Detail

Qualifications

• Substantial experience handling civil litigation in federal court, including motion practice, briefing, and case strategy.
• Demonstrated record of at least 3 successful motions in federal civil litigation, supported by court orders, docket entries, or similar documentation.
• Excellent legal writing, analytical, and verbal communication skills.
• Ability to evaluate legal arguments and translate litigation expertise into clear, actionable feedback.
• Strong understanding of federal civil procedure and litigation strategy.
• Ability to work effectively with cross-functional teams in a remote environment.
• Interest in the intersection of law and technology.

Preferred Qualifications

• Experience with AI, legal technology, or legal training initiatives.
• Experience handling multiple motion types, including motions to dismiss, motions for summary judgment, and discovery motions.
• Experience evaluating or developing legal writing standards and frameworks.

Project Details

• Work Arrangement: Remote
• Engagement: Contractor / Part-Time
• Schedule: Flexible
• AI Experience: Preferred, but not required