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Hospitable — Generous PTO Jobs

Remote-first software that automates short-term rental hosting — guest messaging, pricing and operations for 22,000+ hosts across Airbnb, Vrbo and Booking.com.

5 day week35 days PTOSan Francisco, United StatesMedium (51-200)Fully Remote

About Hospitable

What is Hospitable?

Hospitable builds software "for Airbnbs to rent themselves" — automating guest messaging, task management, reviews and channel connectivity across Airbnb, Vrbo, Booking.com, Agoda and Google Travel. Its mission, in its own words, is "to gift short-term rental hosts their time back." Since 2016 the company has grown "from solving one frustrated host's messaging headaches to more than 22,000 customers worldwide," and now helps 23,000+ hosts manage nearly 27 million guests a year. The funding path is unusual: Hospitable "raised over $2 million directly from our customers and employees, choosing to build alongside our community instead of traditional investors," and says "we've stayed bootstrapped and profitable."

Where will I work?

Wherever you already are. "Hospitable does not have an office or a HQ!" says its public Applicant Handbook. "We are fully remote, fully distributed all over the world." Job ads put it more precisely: "Hospitable.com is a remote-only and fully distributed company. We hire based on timezones, not countries." Today that is "a team of 122 people across 31 countries," and roughly 15% of the team are short-term rental hosts themselves.

What is the Hospitable team like?

Lean and deliberately unlayered. "We grow carefully and intentionally. With a lean team, every role exists because it's genuinely needed... We eliminate unnecessary management layers and bureaucracy." Communication is written-first: "We write things down, keep conversations in public Slack channels by default, and make information easy to find." Transparency is unusually literal here — the company runs a transparent internal compensation grid, and its handbook openly tackles questions like the CEO pay ratio and the gender pay gap. As the careers page warns: "Transparency runs deep. Salaries, financial metrics, and business decisions are shared openly. If this level of openness feels uncomfortable, our environment may not be the right fit." Roles are pitched as "a supportive, radically transparent, and caring team environment, where you are trusted, not managed."

Work-Life Balance

Hospitable publishes its leave policy in full. Every job ad promises "35 days off per year, encouraged (including self-serve public holidays)"; the handbook breaks that into 25 accrued paid vacation days plus 10 days of "bank, public, or religious holidays" chosen by you — "You are not tied to your country's bank holidays... Make your own calendar!" Balances are capped so leave actually gets taken: "We seriously want those vacation days to be taken." Paid sick leave sits outside that allowance. Parental leave is three weeks for birth or adoption, and the handbook candidly admits "we have not yet answered the question of maternity leave in a satisfactory fashion." Focus time is protected by policy: "We value deep work, so we stay mindful of meetings and protect each other's focus time." Nothing Hospitable publishes describes a four-day, 32-hour or compressed week.

Perks and Benefits

  • 25 days accrued vacation plus 10 self-serve public holidays
  • US employees: healthcare including EPO, PPO and HSA plans
  • 401(k) for US-based team members
  • Three weeks parental leave for birth or adoption
  • Free therapists on call through Slack, via Spill
  • Equity as $HOST token RSUs, not tied to location or status
  • Transparent internal compensation grid with salary data shared
  • Remote-only, hired by timezone rather than country
  • Company MacBook Pro provided if needed
  • Company retreats, most recently on the Montenegrin coast
  • Deep work protected; the team stays mindful of meetings

Open Positions

13 jobs