Head of Operations

We're Ooak Data

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.

We are a Y Combinator company with 8 figures contracts signed with frontier AI labs, and we are scaling aggressively over the next months.

🤝 Our values

• Trust, the foundation of every relationship, internal and external. We extend it by default and value the ownership that comes with it.
• Ambition, we commit, we move fast, with tenacity and efficiency.
• Collective, team first, low ego.
• Kindness, at the heart of every interaction.

The offer

📍 Location: Paris (city center), on-site with 1 to 2 days WFH

🕐 Start: as soon as you are available

💼 Contract: full-time (CDI)

💰 Compensation: fixed salary + equity (BSPCE)

✅ Your missions

As Head of Operations, you own the delivery machine: everything that happens between a signed partner and a dataset shipped to a frontier lab. You'll report directly to Grégoire (COO & co-founder) and manage the Ops team.

Your perimeter is the full chain: evaluation → ingestion → anonymization → enrichment → delivery.

• Own delivery end to end. Timelines, quality, and throughput across every dataset we ship.
• Manage and grow the Ops team. You inherit 3 to 4 Ops Managers who already know the machine and are performing. Your job is to make them grow and thrive.
• Own data quality. The QA layer and the annotator workforce sit in your org. You set the quality bar, the way it is measured, and the way it is enforced.
• Industrialize. Much of the chain still takes manual jobs. You redesign it, instrument it, and automate it with the eng and product teams.
• Work with the founders on delivery strategy, capacity planning, and what we can credibly commit to our clients.

📈 What success looks like, first 6 months

• A step change in delivery speed, with the time between a signed partner and a shipped dataset cut dramatically.
• A much lighter cost per delivery: same output, a fraction of the human hours.
• A team that scales without you in the loop: clear ownership & metrics everyone can read.

🔍 Who we're looking for

• 8+ years in operations, delivery, program management, consulting, or a fast-moving startup, with real ownership of a production chain.
• 3+ years managing a team, including senior ICs. This is mandatory.
• A true ops mindset: you think in processes, bottlenecks, cycle times, and unit economics. You measure before you decide.
• An obsession with quality. You have built quality systems, not just quality checks, and you know the difference.
• Deep curiosity, the kind that makes you dig until you actually understand how something works, including the technical parts.
• Serious AI literacy: you understand how models are trained, what RL and post-training are for, and why the data we produce matters. You use AI daily as leverage, not as a toy.
• Automation reflex: you spot repetitive work and turn it into a pipeline. You can script, or vibe-code, or you are hungry to learn fast.
• Fluent English, mandatory (working language with our partners and the labs).

The extras that make the difference

• Experience scaling a data operations or annotation organization.
• Experience working with data or ML engineers, and enough technical vocabulary to arbitrate with them.
• Exposure to privacy, anonymization, or security-sensitive data handling.

🎁 Why join us

• Entrepreneurial adventure: founding impact, live the early days of an ambitious company at the front line of the AI revolution.
• Backed by Y Combinator, join just as we accelerate.
• A team already in place: you are not starting from zero, you are taking a working machine and making it several times bigger.
• Offices in central Paris.
• Perks: Alan health insurance (mutuelle), 50% Navigo covered.

Interview Process

✏️ Recruitment process

We move fast.

• A 30 min intro call with Grégoire (co-founder)
• A 60 min deep dive with Grégoire: your track record, how you run a delivery org, how you lead
• An ops case on scaling the delivery chain, presented to Grégoire and Pierre-Louis (CEO & co-founder)
• A final fit interview with 2 team members
• Reference calls