AI Operations Lead

About Bob W

I’m Bob W, your friend in town. I take the guesswork out of travel, blending the best of both worlds: hotel-grade consistency, local character, and a few surprises only locals would know. Every apartment is fully carbon offset and set up in Europe’s most interesting neighbourhoods, so you feel at home, just with better coffee and smarter tech. I’m building a new kind of stay: five-star comfort, local flair, and always a step ahead on sustainability. All you have to do is show up. I’ll handle the rest.

And now? I’m looking for someone to make my operations a lot smarter.

The Role

We’re a hospitality business using technology to rip up the traditional hospitality rulebook and improve the guest experience. We continuously write and update playbooks, automate tasks, and build tech-enabled systems to deliver that authentic 5-star experience at scale. But right now, AI adoption across the business is unowned. Bobstars (what Bob calls his team) are experimenting independently with Gemini, ChatGPT, and Claude, and no one is responsible for identifying, building, and scaling what actually works. That changes with this hire.

As our AI Operations Lead , you’ll report directly to the COO and work cross-functionally across every department: Engineering, Product, Revenue, Guest Success, Local Operations, Central Ops, Legal, Real Estate, People, and Finance. Your job is not to write strategy decks. It’s to cycle between departments, map what’s actually happening, identify where AI can eliminate manual work, build the solution, document it so it outlasts you, and move on to the next problem.

This is a hybrid role based in Europe with regular travel to Bob W properties. While we value flexibility, we love catching up in person.

Annual Gross Salary: Competitive, depending on experience
ESOP included
Job Level: IC5
Learn more about our career development framework here .

In this role, you will:

• Build and deploy AI-powered automations across revenue management, housekeeping, reporting, scheduling, onboarding, and vendor management; using no-code/low-code tools and APIs (Make, Zapier, Claude, ChatGPT, Mews PMS integrations and more).

• Conduct a comprehensive audit of every department within your first 30 days, mapping current workflows, identifying the biggest manual pain points, and producing a prioritised AI roadmap tied to our Mission.

• Standardise how we use AI tools across the business. Currently, usage is fragmented. Your job is to establish governance, shared tooling, and a framework that works for the whole company, not just individual Bobstars.

• Automate specific high-impact workflows: from lease review and contract processing to monthly reporting cycles, guest communication personalisation, and cross-departmental handoffs.

• Document everything. Every automation ships with a runbook, a named departmental owner, and at least one other Bobstar who can maintain it. If it can’t survive without you, it doesn’t go live.

• Build internal AI literacy across the company: run workshops, create guides, and help Bobstars integrate AI into their own day-to-day. The goal is to upgrade our people, not replace them.

• Report the impact of every initiative to the COO and exec team: hours saved, costs avoided, revenue impacted, and guest experience improvements.

Our 5-star candidate:

• You’re already using AI daily, not as a novelty, but as core infrastructure for how you work. You follow the space closely (think: r/vibecoding, r/ClaudeCode, leading voices on X). You’ve tried Claude Code Max. You have opinions about which models are good at what and why.

• You’ve built things. You can point to automations you’ve shipped that saved real time or money ( in any industry). You’re fluent in no-code/low-code tools (Make, Zapier, n8n, Retool) and comfortable enough with scripting to get unstuck. Actual coding expertise is not required.

• You think in systems. You understand how businesses actually run: the messy reality of cross-departmental handoffs, data living in spreadsheets, and edge cases that break neat workflows. You ask, “Why does this process exist?” before “How do I automate it?”

• You know what not to automate. You can identify what should stay human, and you’re acutely aware of the consequences of a guest-facing automation that breaks at 2 am on a Saturday.

• You document everything you build. An undocumented automation is a liability, not an asset. You build things that outlast you.

• You’re a natural communicator and teacher. You can explain AI to a housekeeper and to a CFO and calibrate accordingly. You get energy from helping other people do their jobs better.

• You’re self-directed. Give you access to the team and the tools, and you’ll find the problems worth solving. You don’t need a detailed brief to get started.

• Industry experience in hospitality is not required. Breadth of problem-solving experience matters more than sector knowledge. Some of the best solutions to our problems have come from completely different industries.

What we’re not looking for:

• A machine learning engineer or data scientist.

• Someone whose primary interest is building or training AI models.

• A consultant who delivers strategy decks and then disappears.

• Someone who wants to automate everything without understanding why a process exists in the first place.

• A generalist with a passing interest in AI. This role requires genuine depth and obsession with the space.

Nice to have:

• Experience in hospitality, proptech, or another operational industry.

• Familiarity with Mews PMS or similar property management systems.

• Exposure to AI governance, data privacy (GDPR), or compliance frameworks.

• Experience participating in or sourcing from AI competitions or hackathons.

• Background in RevOps, BizOps, or operational transformation.

How to stand out:

We’re less interested in your CV and more interested in what you’ve built.

Along with your application, you must submit one of the following (applications without a submission won’t be reviewed):

• A demo, URL, or clear description of an automation you’ve built. What was the problem, what did you build, and what was the measurable impact?

• A walkthrough of a process you looked at and immediately saw how AI could improve it. What would you build, and why?

• Anything that shows you’re the kind of person who says, “This would save us 20 hours a week. Let me build it.”

This isn’t a hoop to jump through. It’s how we find the right person quickly, and how you can tell whether this is the right job for you.

We offer:

• Employee stock option plan (ESOP)

• Unlimited holiday policy

• Free nights and generous discounts at Bob W locations across Europe

• Voluntary health insurance

• Access to the Oliva mental well-being platform

• Sports compensation

• Development and growth opportunities, including a discretionary L&D budget

• Regular team events

• A direct line to the COO and co-founders from day one. This is a high-visibility, high-trust role

• A smart, highly motivated team in a multicultural, diverse, and rewarding work environment

We are an equal-opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.