AI Legal Fellow — Litigation & Motion Practice

Role Title: AI Legal Fellow — Litigation & Motion Practice Job Type: Contractor Location: Remote Job Summary: We are seeking accomplished litigators to join The Winning Motion, a part-time AI fellowship focused on advancing the quality of AI-generated legal advocacy. The fellowship brings together experienced lawyers with strong motion-practice backgrounds to help train and evaluate frontier AI models on one of the hardest remaining problems in legal AI: not simply reaching the right legal answer, but turning sound legal analysis into persuasive advocacy. Fellows will review and evaluate AI-generated motions, identify what separates competent legal writing from exceptional advocacy, and help develop the standards and training data that improve how AI systems frame arguments, use authority, organize facts, and exercise persuasive judgment. We are particularly interested in litigators with a demonstrated record of successful motion practice in federal court and strong instincts for what makes a brief effective before a judge. Key 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. Required Skills and Qualifications: • 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. Preferred 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.