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Legal Expert, AI Model Training

$40 - $125 per hour
Temporary

Crucial Recruiting

Legal Expert, AI Trainer (Remote, Flexible Hours)100% Remote | Work When You Want | Part-Time or Full-Time | Freelance Contract | $40 to $125 per hour


Fully remote. Work when you want. Get paid for what you already know. Applying takes just a few minutes with your resume.
We are partnering with DataAnnotation to find experienced legal professionals to work as remote AI trainers and evaluate how frontier AI models handle real legal work: research memos, contract review and drafting, motion and brief sections, compliance analyses, due diligence summaries and regulatory responses. You bring the judgment you have built marking up a junior's memo and redlining a draft until it is one you would sign. This is project-based, 100% remote work you do from home on your own schedule, alongside a current job, including evenings and weekends.
Already have a DataAnnotation account? This opportunity runs through our partnership with DataAnnotation. If you have already taken a DataAnnotation starter assessment, you are not eligible to apply through this posting. If you created an account but never took the assessment, you can still apply.


What the Work Involves
  • Design realistic tasks from your own practice, such as a research memo on a discrete question, a contract redline with an issues list, a section of a motion or brief, a compliance gap analysis or a due diligence summary
  • Author the supporting files a practitioner would use: agreements, pleadings, correspondence, policies, fact summaries, exhibits
  • Run those tasks through frontier AI models and grade the memo, redline, brief section or analysis they produce
  • Compare two model outputs on the same task and document where each fell short
  • Write grading rubrics covering the right issues spotted, authorities applied and provisions flagged
  • Flag concrete failures: fabricated or misread authorities, wrong standard applied, missed issues, conclusions the facts do not support
Areas of ExpertiseYou need depth in at least one of these, plus enough working knowledge of the others to judge work in adjacent areas:
  • Litigation (civil, commercial, employment or administrative)
  • Corporate and transactional (M&A, commercial contracts, financing)
  • Compliance and regulatory
  • Intellectual property
  • Employment law
  • Real estate or tax law
  • Legal operations with sustained drafting responsibility
Who This Is For
  • 2+ years of legal experience; a current practice is welcome but optional
  • Law degree (JD, LLB or equivalent) preferred. Bar admission valued but not required; senior paralegals and legal analysts with sustained drafting experience are in scope
  • You ground conclusions in primary sources and can tell a real authority from a plausible fabricated one
  • Working knowledge of adjacent practice areas, enough to judge work outside your own
  • Bar admission may be verified during the assessment
  • Hands-on practitioner: you currently do, or recently did, the work yourself as an individual contributor, not solely as a manager
  • Strong written English; you can explain clearly why a result is wrong, not only that it is
  • Familiar with AI tools such as Claude or ChatGPT, with the judgment to tell a well-reasoned answer from a plausible-sounding wrong one
  • Comfortable working independently, following detailed written instructions and incorporating feedback
Pay, Hours and Location
  • Pay: $40 to $125 per hour, depending on project and expertise. Paid via PayPal on a regular schedule. You are paid for every step you complete
  • Hours: Work whenever it suits you, including evenings and weekends. Minimum 10 hours per week with no maximum; full-time hours are available. Multi-day task timers let you spread work across days
  • Location: 100% remote, work from home. Must be based in the United States, Canada, or the UK
  • Tools: Access to the AI models you will evaluate is provided; no personal subscription needed
How to Apply
  1. Apply here with your resume. It takes just a few minutes, and there are no interviews
  2. We review your background against the role
  3. If it's a fit, we send you a link to take DataAnnotation's skills assessment. It's unpaid, takes about 1 to 2+ hours and tests domain judgment and careful reading. The assessment must be entirely your own work; AI-assisted submissions are detected and rejected
  4. If you pass, you complete onboarding and a short training project, then propose and build tasks from your own professional experience, with expert review and written feedback at each stage
Crucial Recruiting and Sidebar Talent are working together on this search in partnership with DataAnnotation via Navaday.
Vacancy posted 3 days ago
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