Chief of staff

Apply on YC · Original job listing

• Role: Finance
• Experience: 6+ years
• Visa: US citizenship/visa not required

The company

Ooak Data turns company data into training data for AI agents.

Frontier labs can train models to reason. They cannot train them to work: navigating a real company's Slack threads, half-finished Notion docs, contradictory Jira tickets, and permission boundaries. That requires real enterprise data, and you cannot synthesize it. You have to source it.

We plug into enterprise tools, anonymize everything into a structurally identical digital twin, and generate reinforcement-learning environments with expert-level tasks calibrated against frontier models. Three weeks from raw company data to an RL-ready environment, three times faster than at launch.

We are a Y Combinator company with signed contracts with three frontier AI labs, and we are scaling delivery aggressively over the next twelve months. Three founders, full-time since December 2025: Pierre-Louis (CEO, ex-COO in edtech, sold data to frontier labs), Grégoire (CPO, first PM at Epsor through Series B), Thomas (CTO, ex-Head of Data at PayLead, ex-Samsung AI lab).

Why this role exists

The three of us are the bottleneck.

Our contracted delivery volume is growing by an order of magnitude. That means more data partnerships to close, more people to hire, more contracts to paper, more cash to manage, and a delivery program that has to run on time across multiple customers simultaneously. Right now all of that lands on three founders who should be spending their time on product, technology, and customers.

We are hiring a Chief of Staff to take the operating company off the founders' desks and run it properly. This is not a support role, and it is not a only a strategy role. It is an ownership role: you will be accountable for whether the company can actually execute.