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This is a fully remote position, open to candidates based in Canada.
Pay: $150–$300/hr
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:
Required Skills and Qualifications:
Preferred Qualifications:
Why Join:
How to apply
Apply here with your profile. We will then email you a link to complete your application on the hiring platform — your application is only considered once that final step is done.
AI Legal Fellow — Litigation & Motion Practice • Toronto, Canada
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