Litigation Associate - Remote

YO AI Labs; Chicago (IL); Remote; USD 83,000 - 165,000; Part time

Job summary

YO AI Labs is seeking an experienced Litigator to serve as an AI Legal Fellow, focusing on federal civil litigation and motion practice. This remote, part-time contractor role supports a project evaluating AI-generated legal advocacy and improving reasoning and writing.

Fellows review AI outputs, provide expert feedback, and help refine litigation strategies while collaborating with cross-functional teams in a remote environment.

Qualifications

• Substantial civil litigation in federal court handling motion practice and strategy.
• Proven ability to craft persuasive briefs with strong authorities.
• Excellent legal writing, analysis and communication skills.

Responsibilities

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

Skills

Motion Drafting

Federal Litigation

Civil Litigation

Federal Court Experience

Civil Procedure

Legal Research & Writing

Trial & Litigation Strategy

Critical Thinking

Attention to Detail

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