Head of Design

About the role

We are looking for our first Head of Design to own the craft, the standard, and the team behind every screen a host touches. Your mission: make Hospitable the best-designed product in short-term rental software—not “good enough for a PMS,” but a product people choose because using it feels effortless. You will build and lead a small team of product designers, and you will keep your own hands on the work. You will report to the CEO, Pierre, whose favorite fruit is Kiwi.

This is a player-coach role, not a manager-of-managers role. If you want to stop designing and only run a team, this isn’t it. If you want to set the bar with your own work and raise everyone else’s, keep reading.

What you will own

The design vision and standard

• Own and set the overall design vision for the product, aligned with the company’s long-term strategy, not just where it is today. Every designer will execute against the direction you set.
• Lead the design of the entire platform and own the quality bar end to end, making every interaction intuitive, every screen elegant, every feature a joy to use.
• Keep shipping. Lead the highest-stakes design work yourself—from discovery and research through prototyping, visual design, and interaction design.

The design system

• Own the design language, style guide, and component library—the system the rest of the team builds within. Keep it coherent as the platform and team grow.
• Reduce complexity as a discipline. Kill inconsistency before it compounds.

The team

• Develop and lead a deliberately lean, AI-leveraged design team and set how design operates here. From day one you’re directing the work, running quality control, and raising the standard of what ships.
• Raise the standard of everyone around you through direct feedback and high expectations—the kind that makes designers do the best work of their careers.
• Partner as an equal with Product and Engineering leadership to decide what we build, not just how it looks.

Data-informed decisions

• Use research, analytics, experimentation, and direct customer feedback to make design calls and prove impact.

Requirements

Hospitable is a remote-only and distributed company. The ideal fit would work in a European or North American (up to East Coast) timezone.

Don’t tick all the boxes? Talk to us about why you’re still an amazing fit. Here’s what we’re paying attention to:

• A design leader who has set the quality bar at a product-led SaaS company within the last 5 years, and raised the standard of the designers around them—through direct feedback, hiring, and high expectations.
• Proven ownership of design direction end-to-end, from discovery through shipped features, with a track record of showing the impact of that work, not just the deliverables.
• Still hands-on. You lead by setting the bar with your own design work, not only by reviewing others’. You’ve kept your hands in the craft in the last 3 years rather than moving to pure management.
• Research and briefing are among your sharpest skills, not just visual polish.
• Strong product thinking: you shape what gets built, and you hold your own as an equal with Product and Engineering leadership.
• High agency and ownership, and comfort getting maximum leverage from a lean setup and modern AI tooling in a remote, low-bureaucracy environment where you’re trusted, not managed.
• You live and breathe in design tools. Nothing exotic: we use Whimsical for mockups, Figma for designs.
• Special kudos if you have short-term rental, travel, hospitality, or proptech domain experience.

When you apply, tell us why this role and this mission. The applications that stand out are the ones that show you actually want to build this, here, with us.

Benefits

The company itself is also a product, one that we iterate on. We’re always improving and creating an environment where we all love to work.

• A supportive, radically transparent, and caring team environment, where you are trusted, not managed—and a culture that is focused on results and output.
• The total cash budget for this role is between USD$171,000.00 to $218,900.00 depending on seniority and the cost of living in your location. We can hire talent internationally as contractors—or employees if you are based in the United States, the European Union, or Australia, taking into account payroll taxes to determine your gross compensation. The gross salary for US employees could be anywhere between $157,619.92 to $201,771.94.
• We al…