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You will design complex legal problems and evaluate AI-generated responses for accuracy, reasoning, and completeness. Your work involves identifying hallucinations, misread clauses, and providing clear rationales to improve AI model performance.
This is an internal role at Weekday. Not a role by a client.
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.
\nAbout 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:
Every task is reviewed. You'll be measured on the quality and rigour of what you submit, not on volume.
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