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.

Read this before you apply

This is not a glamorous role. It's careful, high-volume, detail-obsessed work — and the models we're building are only as good as the data you produce. You'll spend your day looking at documents and drawing bounding boxes around the right things: marking exactly where a field, a block of text, a table, or a signature sits on the page, over and over, correctly. It's precise, repetitive work, and it's the foundation the whole annotation project stands on. One sloppy box teaches the model the wrong thing.

If you get satisfaction from doing something exactly right, at pace, without cutting corners — you'll do well here. If you need constant variety and get bored by repetition, this isn't for you.

What you'll actually do

On any given day you might be:

Looking at documents and drawing accurate bounding boxes around the regions that matter — fields, text blocks, tables, stamps, signatures, whatever the project calls for
Labelling and classifying each box correctly according to the annotation guidelines
Keeping your boxes tight and consistent — same standard on document one and document one thousand
Flagging edge cases, ambiguous documents, and gaps or contradictions in the guidelines instead of guessing
Reviewing and correcting your own (and sometimes others') annotations to keep quality high
Helping refine the labelling process so annotation gets faster and more consistent over time

You'll be measured on accuracy, consistency, and throughput — how much high-quality annotated data you produce, not hours logged.

What we're looking for

You're precise and patient — you can draw the same clean box the hundredth time as well as the first
You sweat the details; a box that's slightly off or a wrong label bothers you
You take ownership. When a batch is yours, it's done right — no follow-ups needed
You follow guidelines closely but speak up the moment something doesn't fit them
You're comfortable with repetitive, screen-heavy work and a Monday–Saturday pace
You care about the quality of your work even when nobody's checking every box

What you get

A front-row look at how a venture-backed startup is built and run profitably
A real understanding of what goes into the data behind AI models — the part most people never see
Real ownership of the ground truth the project depends on
A PPO if you perform
Hands-on experience with the tools and habits that make you genuinely useful anywhere

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.