Virtual Assistant & Executive Assistant (Airbnb / Short-Term Rental Property Management)

About Us

We’re a fast-growing short-term-rental (STR) property-management company that marries hospitality (staykey.com) with technology (prohost.ai). We currently manage 15 properties across multiple time zones, so the daily workload can swing from calm to high-volume depending on occupancy and seasonality. Our obsession: five-star guest stays, clear owner reporting, and relentless process improvement. The Role We need a high-IQ, high-agency Virtual Assistant who will also serve as Executive Assistant to the founders. You’ll cover a 10-hour on-call window, six days per week—handling guest operations when volume spikes and pivoting to executive support and process work during quieter periods. Core Responsibilities Guest Operations (~60 %)

• Monitor Airbnb/STR inboxes and respond within minutes.
• De-escalate issues, coordinate cleaners/maintenance, confirm completion via photo/video.
• Adjust pricing & availability rules in Hostaway, Pricelabs and ProhostAI when occupancy lags.
• Track & dispute reviews, flag reputation risks, draft guest-review replies and submit damage claims to Airbnb. Owner & Team Coordination (~20 %)
• Compile weekly revenue snapshots (revenue, RevPAR, review scores).
• Maintain SOPs in Notion; propose automations for repetitive tasks.
• Handle light bookkeeping: categorize expenses, upload receipts, reconcile payouts. Executive Assistance (~20 %)
• Manage executives’ calendars across three time zones; schedule investor/vendor calls.
• Draft slide decks, one-pagers, and polished emails.
• Run quick-turn research (e.g., local STR ordinance updates, vendor comparisons). Assist with project prioritization and ticket management for ProhostAI customers. (Percentages flex with guest volume—expect surges on weekends and holidays, and lighter stretches during low-season weeks.) Must-Have Qualifications
• 2+ years VA experience in STR or hospitality—you know back-to-backs, gap nights, and response-time metrics.
• Fire-tested problem solver who owns outcomes without hand-holding.
• Flawless written English and confident spoken English on calls.
• Tool-stack fluency: Slack, Hostaway (or similar PMS), ProhostAI, Intercom, Linear, Notion, Google Workspace, Zoom. Expert in Airbnb policies and knows their way around VRBO, Booking.com and Expedia.
• Time-zone reliability: able to hold a consistent 10-hour on-call window overlapping 9 a.m.– 9 p.m. ET or PT.
• High agency & curiosity: you spot inefficiencies and fix them before they become problems.

Nice-to-Have

Extras

• Prior bookkeeping or property-management accounting experience.
• Experience supporting C-suite or startup founders.
• Comfort configuring lightweight automations in Zapier. Success Metrics (First 90 Days)
• ≥ 95 % guest-response rate within 5 minutes.
• Zero missed escalations; all critical incidents resolved or handed off with context.
• At least two documented process improvements that save > 5 hours/week. Compensation & Benefits
• Compensation: $500-$1400/month depending on experience. 13th month pay.
• Paid time off: 7 days per year
• Fast-track growth into Ops Manager or Chief of Staff for standout performers.

How to Apply

• Submit your application on this portal
• Attach your résumé and a one-page cover letter together in one PDF file that includes:
• A specific guest crisis you solved independently.
• A metric you improved and how you did it.
• Record a one-minute video intro (phone video is fine). Briefly tell us who you are, your proudest STR win, and why you thrive in high-velocity environments. Upload it to an unlisted YouTube or Loom link and include the URL in your job application.
• Complete our 60-minute logic & scenario assessment at this link.
• Please note that your application will be considered only after completing both parts of the application listed above. Applications are reviewed on a rolling basis—early applicants get priority. If you love making complex operations hum and enjoy wearing many hats, we’d love to meet you. Created at 2025-07-10 17:43:25 Updated at 2025-10-09 21:48:40 Location: Remote (International); About ProhostAI: Why You Should Join ProhostAI ProhostAI (YC S24) building an AI-powered operating system for Airbnb & short-term rental hosts. Our founding team consists of data scientists and engineers from Airbnb, Dropbox, Twitter and Harvard. We are backed by Y Combinator, Pear VC, Pioneer Fund, Data Tech Fund and others. Our founding team comes from Airbnb and Dropbox engineers and data scientists who are also hosts with a 4.99+ rating across thousands of stays. companyDescription: ProhostAI (YC S24) building an AI-powered operating system for Airbnb & short-term rental hosts. Our founding team consists of data scientists and engineers from Airbnb, Dropbox, Pinterest, Harvard and Yale. We are backed by Y Combinator, Pear VC, Pioneer Fund, Data Tech Fund and others. Our founding team comes from Airbnb and Dropbox engineers and data scientists who are also hosts with a 4.99+ rating across thousands of stays. More about this company: positions:
• ProhostAI - Founding Engineer - Full Stack
• ProhostAI - Founding Engineer, iOS
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