Head of People

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.

The Role

Hospitality is a people business. At Bob W, that isn't a fluffy statement in the employee handbook; it's the operating model: the five-star experience our guests feel is built and delivered by the people we hire, develop and retain. The People team shapes the product, not just supports it.

As Head of People, you'll lead the most senior People position at Bob W, on the management team, reporting to our COO, who held this role himself for the past two years. You'll steward and evolve our culture as we scale across Europe. We're currently 250 people. We don't measure the business on headcount growth, but our recruitment team is always busy, so you can draw your own conclusions about the pace 😉

You'll bring People leadership, a track record of building complex functions from scratch, a commercial head, and a healthy dose of empathy.

The role is Tallinn-based. We prefer people who want to spend the majority of the week in the office with the team, though there are no mandated office days. We won't be able to consider applications from outside the EU, or from anyone unwilling to relocate to Tallinn.

Start date: January 2027
Job Level: M5 (of 8).
Salary range: €55,000 - €70,000, depending on experience.

What success looks like

In your first year, you'll have overhauled our compensation framework, 360 feedback, and performance review process, thoughtfully integrated AI and automation into our People processes in a way that enhances the experience for Bobstars and candidates, not dehumanises it, and improved how we serve our Bobstar colleagues day-to-day. Beyond that, the sky is the limit.

In this role, you will

• Lead and grow our People function, including People Ops, Office Management and Recruitment, into a lean, mission-driven team.
• Embed our values across every people process and partner with leaders to evolve the culture.
• Own People operations end-to-end: recruitment, onboarding, L&D, total rewards, employee relations and compliance.
• Build scalable frameworks for career development and compensation, and a best-in-class L&D programme that drives growth and retention.
• Partner with senior leadership on strategy and organisational design across the business.
• Own the People strategy for M&A and new market launches, and keep us compliant with local labour law across every market we operate in.

Our five-star candidate

• Has led People at a senior level in a high-growth, international business, and has built and scaled teams and processes from the ground up.
• Has owned the People function across multiple countries and legal entities, supporting cross-border teams.
• Is comfortable dealing with jurisdictional employment law, resolving matters internally and working with outside counsel where needed. We don't expect you to know the law in all 10+ of our markets cold, but you should get up to speed fast.
• Balances strategy with hands-on execution, especially in a lean team, and navigates ambiguity and change without losing the plot.
• Communicates with empathy, clarity, and confidence; coaches rather than commands; and builds trust at every level.
• Is fluent in English (other languages a bonus) and authorised to work in Estonia.

What does the interview process look like?

• Introductory interview with the hiring manager, our COO (45 min)
• In-office workshop with the People Team (90 min)
• Final interview with our Co-founders (45-60 min)

We offer

• The chance to reinvent the world's largest industry inside a young company with big ambitions.
• Employee stock option plan.
• Unlimited holidays.
• Free nights and generous discounts at Bob W locations.
• Health insurance.
• Sports compensation.
• Access to the Oliva mental well-being platform.
• Top-notch Apple hardware.
• An L&D budget and real room to grow.
• Regular team events.
• A smart, motivated team in a multicultural and genuinely rewarding place to work.

Please note that this position will be closed as soon as a sufficient number of qualified candidates are identified. We encourage interested applicants to submit their applications promptly.

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.