AI Legal Fellow — Litigation & Motion Practice

About the role

The Winning Motion is a part-time AI fellowship focused on advancing the quality of AI-generated legal advocacy. We are seeking accomplished litigators to join as contractors (remote) to review and evaluate AI-generated motions, identify what separates competent legal writing from exceptional advocacy, and help develop standards and training data that improve how AI systems frame arguments, use authority, organize facts, and exercise persuasive judgment.

Responsibilities

• Perform simulated motion drafting, briefing, and litigation strategy exercises.
• Review and assess AI responses to litigation scenarios, providing expert feedback to improve model performance and output precision.
• Create objective evaluation frameworks and grading criteria to assess AI performance on litigation tasks with rigor and consistency.
• Collaborate with product and research teams to refine data, guidelines, and best practices for AI-driven litigation support solutions.

Requirements

• Substantial experience litigating civil matters in federal court, including motion practice, briefing, and case strategy.
• A record of at least 3 motions won in federal civil litigation, with supporting documentation (e.g., court orders or docket entries) required.
• Exceptional written and verbal communication skills with meticulous attention to detail.
• Strong analytical capabilities and ability to translate legal expertise into actionable feedback for AI systems.
• Demonstrated commitment to innovation at the intersection of law and technology.
• Experience working with cross-disciplinary teams in fast-paced environments.

Qualifications

• Prior exposure to AI, legal tech, or training initiatives.
• Experience across a range of motion types (e.g., motions to dismiss, summary judgment, discovery motions).

Why Join

• This is an opportunity to work at the intersection of law and technology.
• You will help define how AI is developed for a new generation of legal practitioners.
• You will apply your courtroom experience in a high-impact research environment.