Head of Design

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.

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, this is the role.

The ideal fit would work in a European or North American (up to East Coast) timezone.

• 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
• Fluent with Whimsical and Figma
• Special kudos if you have short-term rental, travel, hospitality, or proptech domain experience