Commercial Litigation AI Evaluation Attorney

About Open Train

Open Train is the #1 platform for finding and building careers in AI training and data labeling. We help specialists discover meaningful projects, present their expertise clearly, and build a portable record of high-quality contributions.

In this role, Open Train AI is hiring and contracting with an experienced attorney to apply practical litigation judgment to the development and evaluation of artificial intelligence systems.

• Remote contractor engagement
• Part-time schedule of 20 or more hours per week
• Hourly compensation of $100 to $150 USD
• Open to candidates located in the United States

AI training is the human side of building modern artificial intelligence. Legal experts help AI systems improve by creating realistic examples, reviewing generated work, identifying errors, and explaining what strong reasoning and professional-quality output should look like.

Your litigation expertise will help translate complex legal judgment into scenarios, evaluation standards, and feedback that clarify how an AI system should reason across the litigation lifecycle.

• Work directly on cutting-edge AI training and evaluation
• Apply professional expertise to realistic legal simulations
• Prior AI experience is not required
• Contribute using public or synthetic materials only

Open Train is seeking a Commercial Litigation AI Evaluation Attorney to design and evaluate realistic commercial dispute simulations. You will create case scenarios, guide legal contributors, assess work product, and develop standards for evaluating AI performance at each stage of a dispute.

The engagement is designed for experienced US litigators who can assess complex legal analysis without relying on confidential client materials. You will collaborate with legal peers and team leads as scenario requirements develop.

• Create realistic commercial litigation scenarios and legal work products
• Evaluate AI-related legal analysis against professional standards
• Help define how strong litigation reasoning should be assessed
• Use no client-confidential information

You will turn practical litigation judgment into structured simulations and actionable evaluation guidance. The work includes both independent legal analysis and direction of junior and peer-level contributors.

• Draft multi-turn scenarios with facts, parties, legal issues, procedural posture, and initiating documents
• Direct junior legal contributors producing briefs, motions, discovery strategy documents, and demand letters
• Review junior and peer-level work as a neutral evaluator
• Maintain a high professional standard across each stage of a dispute simulation
• Create and refine rubrics for pleadings, discovery, motions, hearings, and resolution strategies
• Identify ambiguities, edge cases, and procedural complexities that may challenge AI performance
• Provide clear, actionable feedback on legal work and reasoning
• Collaborate with legal peers and team leads as requirements evolve

This role requires substantial hands-on US litigation experience and the ability to evaluate and direct legal work without personally redrafting it. Candidates must meet the following requirements.

• Admission to a US bar in at least one jurisdiction, whether active or lapsed
• At least 10 years of hands-on US litigation experience
• Experience with courtroom advocacy, discovery, motion practice, and case-team leadership
• Deep expertise in commercial contract disputes, shareholder or LLC disputes, or commercial real estate litigation
• Strong command of the full litigation lifecycle
• Formal legal drafting expertise
• Excellent written and verbal communication
• Strong adversarial reasoning
• Ability to evaluate legal work neutrally and develop litigation-stage success rubrics

Experience across multiple commercial litigation domains and prior collaborative calibration with other legal experts will help you contribute effectively. Prior AI training or evaluation experience is not required; the central skill is translating established litigation expertise into clear benchmarks and realistic scenarios.

• Experience spanning multiple commercial litigation domains
• Experience calibrating evaluations with other legal experts
• Interest in improving the reliability and capabilities of AI systems

This is a remote, part-time contractor engagement for candidates in the United States, with an expected commitment of 20 or more hours per week. Work must be completed with public or…