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AI Legal Fellow — Litigation & Motion Practice

$150–$300/h

Remote

Role overview

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:

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


Required Skills and Qualifications:

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


Preferred Qualifications:

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


Why Join:

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

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Future of work · September 2026

How big is the remote / hybrid opportunity?

Remote work is already huge — but the bigger story may be the hundreds of millions of jobs that could still move beyond geography.

Sporterer Insights · Approximate figures based on World Bank and ILO estimates
Global remote and hybrid work opportunity infographic

Remote work already connects millions of people with companies they would never have been able to work for a decade ago. But compared with the size of the global labour market, it may still be early.

The interesting number is not only how many people work remotely today — it is how many roles could plausibly become remote or hybrid next.

The chart above starts with roughly 3.3 billion people employed worldwide. Around 300 million jobs are already remote or hybrid, while an additional pool of roughly 250 million roles could potentially move in that direction as technology, workflows and company culture continue to change.

Skills are becoming more portable

This matters because more work can increasingly be matched to expertise rather than location. AI training and evaluation are a good example: companies need lawyers, engineers, designers, editors, researchers, finance professionals and many other specialists to help improve AI systems.

For workers, that creates access to projects outside their local market. For companies, it expands the talent pool from one city or country to the world.

Explore remote opportunities →