Legal Expert – AI Training & Evaluation

Weekday (YC W21)

. Design complex legal problems, including research questions, contract analyses, and compliance scenarios, with clear, defensible model answers .

Posted 10/9/2026contractRemote • IndiaMid-LevelSenior💰 ₹20,000 - ₹25,000 per weekWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in legal research, contract analysis, and regulatory compliance, with a strong focus on precision in writing and analytical reasoning. Capable of evaluating AI-generated legal responses and providing clear rationales for assessments.

Highest-signal resume keywords

Legal ResearchContract AnalysisRegulatory ComplianceAnalytical SkillsPrecision in Writing

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Legal ResearchContract AnalysisRegulatory ComplianceLegal ReasoningEvaluation of AI Responses

Soft Skills

Attention to DetailReliability on DeadlinesCuriosity about AI

Industry Keywords

Legal ExperienceCompliance ScenariosModel AnswersQuality StandardsDefensible Rationale

About the role

Key responsibilities & impact

Design complex legal problems, including research questions, contract analyses, and compliance scenarios, with clear, defensible model answers
Review AI-generated legal responses line by line and grade accuracy, reasoning, and completeness
Identify hallucinated case law, misread clauses, missed exceptions, and flawed reasoning
Write clear rationales explaining evaluation results
Work across legal research, contract analysis, regulatory compliance, and legal reasoning
Submit work that meets quality and rigour standards; tasks are reviewed and measured on quality rather than volume

Requirements

What you’ll need

3+ years of relevant legal experience — in practice, in-house, or at a firm
Strong legal research and analytical skills
Ability to trace a question to the right authority and explain why it applies
Comfort with contracts, compliance, and reasoning across more than one area of law
Precision in writing
Low tolerance for plausible-sounding nonsense
Reliable on deadlines
Curiosity about how AI is going to change legal work
Preference for shaping AI development over watching it happen

Benefits

Comp & perks

Remote, flexible work you can fit around a practice or a full-time role
Front-row seat to how frontier AI models are trained and evaluated on legal work
Opportunity to help improve frontier AI models
YC-backed team that moves fast and keeps things direct
More tasks and larger projects if your work is consistently strong