Virtual Assistant - Guest & Property Operations

Virtual Assistant – Guest & Property Operations
Schedule: 30 hours per week (Evenings + Alternating Weekends, with path to Full-Time)
Rate: $7–$9/hour (based on experience)
Start: Early May

About the Role

We’re looking for a proactive, detail-oriented Virtual Operations Assistant to take full ownership of
guest communication and property operations for a growing short-term rental portfolio.

This role is not just support—you will act as the primary point of contact for guest messaging, replacing a third-party messaging service. You’ll be responsible for delivering fast, thoughtful, and context-aware communication that drives 5-star guest experiences.

In addition to messaging, you will support backend operations including vendor coordination, maintenance tracking, supply ordering, and listing support.

This is a high-impact role with strong potential to grow into full-time as the business scales.

Schedule
• Wednesday–Sunday: 5:00 PM – 12:00 AM (Central Time)
• Break: one-hour unpaid break per shift
• 30 hours per week (with path to full-time)
• Regular short check-ins (e.g., 15-min daily/weekly syncs initially) to align on decisions and training
Note: Mondays and Tuesdays are off-days as the owner handles coverage during those slower periods.

Key Responsibilities
Guest Communication & Escalations (Primary Focus)
• Manage end-to-end guest messaging across platforms
• Respond promptly with context-aware, friendly, and professional communication
• Handle inquiries, issues, special requests, and complaints
• Ensure excellent guest experience and maintain brand tone
• Identify patterns and create templated/automated responses to improve efficiency

Bookings & Calendar Management
• Keep calendars accurate across platforms
• Process booking adjustments and updates in real time

Automation & Process Optimization
• Set up and refine auto-responses and messaging workflows
• Use AI/tools to streamline communication
• Continuously improve systems based on recurring scenarios

Maintenance & Vendor Coordination
• Log and track issues in systems like Breezeway
• Coordinate with vendors (cleaners, maintenance, etc.)
• Ensure timely resolution of issues

Cleaning & Turnover Oversight
• Monitor schedules and ensure properties are guest-ready
• Communicate with cleaning teams as needed

Listings & Onboarding
• Assist with drafting and uploading new listings
• Support onboarding of new properties into systems

Ordering & Inventory
• Order supplies (e.g., via Amazon)
• Track inventory and anticipate needs

Administrative & Operational Support
• Maintain internal documents, trackers, and SOPs
• Organize files and systems
• Assist with light reporting and operational tasks

Qualifications
Required
• 2–4+ years experience in short-term rental/Airbnb operations or property management
• Hands-on experience with tools like Breezeway, Hospitable, Turno, or similar (exact tool less
important than quick learning)
• Outgoing, friendly, and engaging communicator (critical for guest-facing role)
• Proactive and takes ownership of responsibilities
• Systems-oriented and comfortable improving workflows
• Able to think critically and make decisions with minimal oversight
• Proven vendor coordination and escalation handling
• Excellent written/verbal English; professional, guest-focused communication
• Highly organized with strong follow-through and attention to detail
• Comfortable with U.S. evening/weekend hours (night shift experience a plus)

Preferred
• Experience launching/optimizing new STR listings
• Familiarity with Wrike or similar project management tools
• Leadership/project management mindset or experience training others
• Background improving SOPs/workflows in growing operations
• Ability to thrive in ambiguity while seeking guidance early

To apply, kindly fill out this form:
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