Head of People

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

We were 4 in June. We are 16 today, and we should be around 25 by Christmas.

So far every hire has been screened, often sourced, and always closed by one of the three of us. We loved doing it. But at this pace it pulls us away from product, engineering and customers, and it makes us slower to answer people than we want to be.

Speed matters. What matters more is who we become. The team we build over the next twelve months is the company. Every hire either strengthens what we stand for, trust, ambition, collective, kindness, or quietly waters it down. Someone has to hold that line with us: in who we go after, in the hard calls, in how people are welcomed, how they grow, and why they stay.

We are looking for a Head of People to build that team with us. The one people will want to join, and grow in.

What you will own

Hiring, end to end

• 10+ hires in your first six months across tech, ops and GTM, found and closed in-house: ML engineers, data engineers, a product manager, sales, ops.
• You hunt. Cold outreach, referrals, communities, whatever finds the right person. Agencies when it helps, never as a crutch.
• You close, against counter-offers, big-tech comp and plain inertia. And you co-own the bar with us: who we hire, who we don't, and why.
• You keep it fast and humane. Board clean, interviewers prepped, every candidate answered within 48 hours. People should enjoy the process even when the answer is no.

Employer brand

• Careers page, YC Work at a Startup, content, events. Make Ooak the place AI-curious people want to work.

The team we become

• Turn our values into how we actually work: how we give feedback, how we decide, how we welcome someone on day one, how we say goodbye when we have to.
• Help us make the hard people calls, and make sure they are made with care.

The people foundation

• The BSPCE plan and the salary grid, and their yearly refresh.
• Payroll coordination with our accountant, France and US, employees and freelancers.
• Onboarding, feedback cadence, reviews, and the rituals that keep 25 people feeling like one team.

Who you are

You have done this before. You have run People in a startup or scale-up that grew fast while you were there, and you know what crossing 50 people does to a company. Maybe you built the function from a blank page, maybe you scaled one. What matters to us: you have closed hard profiles yourself, and you have stayed close to a team through the good weeks and the hard conversations.

• You see People as a lever for the business, not a support function. You know what a decision really costs before you advise against it, and you can tell real risk from theoretical risk.
• You have worked directly with founders, and you tell them what they don't want to hear, kindly and with reasons. You are right often enough that we listen.
• You have built a culture. Somewhere there is a company where the values showed up in everyday decisions because of you.
• You listen. Friction, unspoken needs, the mood of the place: you pick it up before it becomes a problem.
• You give trust first, and you are demanding on what follows: deadlines, contracts, process.
• Kind, not soft. Honest feedback, hard conversations, and warmth in how you deliver both.
• You can build and run a team, in-house and with the right partners.
• Curious about AI. You use it every day, and you actually want to understand what we build.
• 8+ years in People or Talent. Fluent French and English, ideally with a multi-country story behind you. Based in Paris.

And you want to give a lot to build an ambitious, fast-growing company where people are glad to come in on a Monday.

Bonus points if you have hired for an AI or data company and know what a good ML engineer looks like on paper and in a call.

Terms

• Compensation: €70-90k + bonus, and 0.2% to 0.5% BSPCE depending on profile.
• Location: Paris, on-site with 1 to 2 days WFH.
• Start date: as soon as you can.
• Perks: Alan health insurance, 50% Navigo.