Villa Paraiso Vacation Rentals manages about 20 luxury vacation homes in the Florida Keys and Miami. We run a lean, AI-first operation, and we're hiring a long-term Operations Administrator to run the day-to-day and make it run better every week. You'll work directly with the founder. This is not a VA or call-center role.
What you'll own:
- Daily operations: reservations, arrivals and departures, guest communication, and cleaning and maintenance coordination, handled accurately and on time.
- Records and admin: calendars, property details, vendor and owner records, task notes and follow-ups, kept clean and current.
- Workflows and automation: find repeated work and build the template, checklist, or automation that removes it, using AI and no-code tools.
- AI in practice: use AI every day to draft, summarize, triage, and review work, with human judgment on anything that matters.
- Documentation: write and maintain the SOPs other team members follow.
- Escalation: raise refunds, damage, safety issues, and policy exceptions early, with the facts already gathered.
Success looks like:
- 30 days: you know the homes, the tools, and our standards, and you handle routine operations with review.
- 90 days: you run the daily rhythm on your own and have shipped at least two workflow improvements.
- 6-12 months: you're a trusted operator, owning broader decisions and growing toward operations manager as we add homes.
Requirements:
- 2+ years in operations for short-term rentals, property management, hospitality, or a small business, owning outcomes rather than just carrying out tasks.
- Fluent written and spoken English.
- AI-native: you already use ChatGPT, Claude, or similar every day to draft, summarize, research, and check work, and you verify facts before anything goes out.
- You have built at least one real workflow or automation (Zapier, Make, n8n, Google Apps Script, Airtable, PMS automations, or similar) and can show it.
- Systems thinking: when the same problem happens twice, you fix the checklist, template, or automation that caused it.
- Clear SOP writing, clean records, and closing the loop on every task.
- Reliable computer, quiet workspace, primary internet plus a mobile backup.
Strong plus:
- Guesty, Hostaway, or another PMS; Breezeway or other turnover software.
- Spreadsheets beyond the basics: lookups, pivots, simple dashboards.
- Owner reporting or month-end support.
- Some API or light scripting experience.
- Spanish.
Tools: Guesty, Breezeway, Slack, Google Workspace, AI assistants, and whatever you build on top of them.
Pay and time tracking: USD $8-13/hour depending on experience. Hours are tracked in Hubstaff.
