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Hospitable in the short-term rental software space is seeking a First Head of Design to own the craft, style, and team behind every host-facing screen. This player-coach role balances hands-on design with building a small team, reporting to the CEO.
You will shape discovery to shipped features, establish the design language, and drive a lean, AI-enabled process across time zones. The ideal candidate has recent experience leading design at a product-led SaaS company, with a track record of
First Head of Design role owning the craft, the standard, and the team behind every screen a host touches. Mission: make Hospitable the best-designed product in short-term rental software. Role type: player-coach role, not a manager-of-managers role;
requires buildingand leading a small team of product designers while keeping hands on the work. Reporting: reports to the CEO, Pierre, whose favorite fruit is Kiwi.
Own and set the overall design vision for the product, aligned with the company's long-term strategy. Lead the design of the entire platform and own the quality bar end to end, making every interaction intuitive, every screen elegant, and every feature a joy to use. Lead the highest-stakes design work yourself— from discovery and research through prototyping, visual design, and interaction design. Own the design language, style guide, and component library. Reduce complexity as a discipline and kill inconsistency before it compounds.
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. Hands-on experience, having kept hands in the craft in the last 3 years rather than moving to pure management. Sharp skills in research and briefing. Strong product thinking to shape what gets built 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. Proficiency in Whimsical for mockups and Figma for designs. Ability to work in a European or North American (up to East Coast) timezone.
Short-term rental, travel, hospitality, or proptech domain experience.
Total cash budget: USD$171,000.00 to $218,900.00 depending on seniority and the cost of living in your location. International hiring: available as contractors or as employees if based in the United States, the European Union, or Australia. US employees gross salary: $157,619.92 to $201,771.94.
Equity: compensation includes company equity through RSUs, with a current grant value of up to $119,400.00.
Performance: eligible for up to an additional $671,637 per year in Performance Share Units (PSUs), granted upon the achievement of clearly defined business performance targets. US benefits: healthcare (including EPO, PPO, and HSA) and 401(k).
Time off: 35 days off per year (including self-serve public holidays) and parental leave. Mental health: complimentary mental health and emotional support with therapists on call through Slack.
Recognition: peer recognition platform to earn virtual coins redeemable through gift cards, donations, or monetary rewards.
Builds software for short-term rentals to rent themselves, with a state-of-the-art product and user experience. Remote-only, global, and trust-based company. Applicant Handbook: https://hsptb.Com/hndbk Public Town Halls: https://hsptb.Com/twnhll