Legal Expert - AI Training & Evaluation at Weekday AI (YC W21) in IN

This is an internal role at Weekday. Not a role by a client.

• Role type: Project-based / Contract
• Location: Remote
• Compensation: ₹20,000–25,000 per task
• Experience: 3+ years as a practising lawyer or legal professional
• Hours: Flexible and task-based — no fixed working days

Weekday is an AI-native recruiting platform. We are backed by Y Combinator and Venture Highway (now General Catalyst). We have built the largest white-collar talent database in India and have built tools to run outbound recruiting campaigns to them.

We are now running an AI training and evaluation project as a YC-backed AI data lab, and we're looking for legal experts to build and judge the tasks that advanced AI models get tested on.

About the role

Advanced AI models are being pushed into legal work — research, contract review, compliance. Whether they're actually any good at it depends on the quality of the people who train and test them. That's you.

You'll create complex legal tasks that a model should be able to handle but often can't, and you'll evaluate what the model produces — where it's right, where it's subtly wrong, and where it's confidently making things up. The work rewards precision. A vague task or a lazy evaluation is worse than none at all.

This is not paralegal work and it's not data entry. Each task is a piece of real legal thinking — the kind of question a senior associate would be asked and have to get right. If you want templated, repetitive work, this isn't for you. If you like taking a hard legal problem apart and explaining exactly why an answer is wrong, you'll probably enjoy it.

What you'll actually do

On any given task you might be:

• Designing a complex legal problem — a research question, a contract to analyse, a compliance scenario — with a clear, defensible model answer
• Reviewing AI-generated legal responses line by line and grading them on accuracy, reasoning, and completeness
• Catching hallucinated case law, misread clauses, missed exceptions, and reasoning that sounds right but isn't
• Writing clear rationales for your evaluations so the model (and the team) learns from them
• Working across legal research, contract analysis, regulatory compliance, and legal reasoning — not just one niche

Every task is reviewed. You'll be measured on the quality and rigour of what you submit, not on volume.

What we're looking for

• 3+ years of relevant legal experience — in practice, in-house, or at a firm
• Strong legal research and analytical skills. You can 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. You say exactly what's wrong and why, without padding
• Low tolerance for plausible-sounding nonsense — from a model or anyone else
• Reliable on deadlines. Task-based work only works if the tasks come back on time
• Curiosity about how AI is going to change legal work, and a preference for shaping it over watching it happen

What you get

• ₹20,000–25,000 per task — paid for depth of thinking, not hours logged
• Remote, flexible work you can fit around a practice or a full-time role
• A front-row seat to how frontier AI models are trained and evaluated on legal work, and a hand in making them better
• A YC-backed team that moves fast and keeps things direct
• More tasks and larger projects if your work is consistently strong