Contract Playbook General Counsel

About OpenTrain

OpenTrain AI is the #1 platform for people building careers in AI training and data labeling. We connect experienced contributors with document-driven projects that teach and refine AI systems, and we help professionals consolidate work and grow durable freelance careers.

OpenTrain AI is the hiring and contracting organization for this role. Creating an OpenTrain account is free and lets you apply, manage work, and build a portfolio of AI-training contributions.

About AI Training Work

AI training (data labeling/annotation) is the human side of building modern AI. Experts prepare and review documents, annotate content, and provide feedback that models learn from—work that directly shapes how systems understand contracts, language, and legal risk.

This role is document-driven: your legal drafting and annotated examples will be used to teach models text generation and to create evaluation criteria that ensure consistency and reduce downstream legal risk.

The Role

OpenTrain AI is hiring a Contract Playbook General Counsel to create, review, and refine contract negotiation playbooks, draft and annotate commercial agreements, and recommend template improvements. You will produce concise written and verbal guidance designed to teach AI systems and inform human reviewers.

This is a part-time contractor role (20+ hours/week), fully remote and open worldwide. Work language: English. Compensation is hourly: $90–$130 USD per hour. You must hold active bar membership and state licensure to practice law.

• Employment type: Contractor, Part-time
• Time commitment: 20+ hours/week
• Pay: $90–$130 USD per hour
• Work language: English; worldwide applicants eligible

What You Will Do

Your work is centered on real contract documents and negotiation scenarios. You will turn real-world practice into clear playbooks and annotated training materials that improve contract clarity, efficiency, and risk outcomes.

• Build and refine contract negotiation playbooks from real scenarios and company requirements
• Draft, analyze, and annotate commercial agreements with attention to clarity, precision, and compliance
• Evaluate existing contract templates and recommend changes that reduce risk and speed negotiation
• Curate non-confidential transaction materials to support documentation and training objectives
• Provide concise, actionable feedback on contract management and negotiation practices

Requirements

Candidates must bring hands-on commercial contracting experience and the ability to convert that expertise into teachable, document-level guidance for reviewers and models.

• Current or prior experience as General Counsel, Deputy General Counsel, or Assistant General Counsel
• Strong background in commercial contract drafting, negotiation, and contract management
• Familiarity with contract playbooks, template optimization, and practical risk assessment
• Excellent written and verbal communication with meticulous attention to detail
• Active bar membership and state licensure to practice law (bar number required)

Who Should Apply

Apply if you enjoy translating practical legal judgment into repeatable guidance, producing annotated documents, and helping shape how AI systems learn to handle contracts. This role suits senior in-house or private-practice counsel who want part-time, remote work that impacts AI tools and human reviewers alike.

No specialized labeling platform experience is required—strong contract experience and the ability to write clear annotations and playbooks are the core needs.