Guest Experience Representative

Luxury Short-Term Rental Property Management
Ontario, Canada & Select Texas Markets (Remote Position)

About Us

We are a premium property management company specializing in luxury short-term rentals across Ontario, Canada and select markets in Texas. Our portfolio consists of high-end, design-forward homes that deliver exceptional, five-star guest experiences. We operate with a hospitality-first mindset and a strong operational backbone that ensures consistency, quality, and performance.

We are looking for a highly responsive, detail-oriented, and experienced Virtual Assistant who thrives in a luxury short-term rental environment and understands what it takes to consistently maintain 5-star performance metrics.

Position Overview

The Virtual Assistant plays a critical role in protecting our brand standards, guest satisfaction, and revenue performance. This role requires someone who is proactive, decisive, organized, and capable of managing guest communication, operations, and maintenance coordination in real time.

You will act as the front line of guest communication while also overseeing property readiness, vendor coordination, platform case management, and pre-check-in quality control.

This role is performance-driven and KPI-based.

Core Responsibilities

1. Five-Star Guest Communication

* Provide polished, professional, and brand-aligned guest communication
* Respond to all guest messages within 5 minutes during scheduled working hours
* Manage inquiries, booking requests, and direct bookings
* De-escalate guest concerns quickly and effectively
* Ensure guests feel supported before, during, and after their stay


2. Platform & Systems Management

Required proficiency in:

* Hospitable
* Airbnb
* VRBO
* Turno
* ChatGPT (for efficiency, drafting responses, and workflow support)

Responsibilities include:

* Managing calendars and reservations in Hospitable
* Facilitating direct bookings
* Automating and monitoring guest messaging workflows
* Coordinating turnovers using Turno
* Managing listings and reservations across Airbnb and VRBO
* Utilizing ChatGPT to enhance communication quality and operational efficiency


3. Airbnb Case & Claims Management
• Liaise directly with Airbnb representatives for:
Damage claims
Guest disputes
Refund negotiations
Resolution center cases
• Provide proper documentation and follow-up
• Protect revenue and minimize unnecessary refunds
• Must have a proven track record of successfully working with Airbnb representatives

4. Property Readiness & Quality Control

* Work in real time with on-site property inspectors via video calls
* Conduct virtual pre-check-in inspections to ensure properties meet 5-star standards
* Verify cleanliness, staging, inventory levels, and overall presentation
* Identify deficiencies before guest arrival
* Ensure any issues are resolved immediately prior to check-in


5. Cleaner & Maintenance Coordination

* Build and maintain strong working relationships with cleaning teams and maintenance providers
* Ensure turnovers are completed on time and meet luxury standards
* Proactively identify and address potential maintenance issues
* Coordinate urgent repairs when necessary
* Track recurring issues and implement preventative solutions
* Maintain inventory and supply standards


Key Performance Indicators (KPIs)

This is a performance-based role. Success is measured by:

* Consistent 5-star reviews
* 5-star cleanliness ratings
* 5-star communication ratings
* Zero avoidable refunds issued
* Zero inventory issues (no supplies run out)
* Minimal guest complaints
* Successful claim recovery for damages

Maintaining luxury-level consistency across all properties is non-negotiable.

Qualifications

* Proven experience managing short-term rentals (luxury portfolio preferred)
* Demonstrated success working with Airbnb representatives and the resolution center
* Strong written English communication skills
* Exceptional response time discipline
* Experience managing multiple properties simultaneously
* Strong problem-solving and decision-making skills
* Ability to remain calm under pressure
* High level of accountability and ownership


Ideal Candidate Profile

* Hospitality-obsessed and guest-experience driven
* Extremely detail-oriented
* Process-driven and organized
* Proactive rather than reactive
* Comfortable working across Ontario and Texas time zones
* Strong sense of urgency
* Protects brand reputation and revenue at all costs


Work Structure

* Remote position
* Required availability during high-volume guest communication hours
* KPI-driven performance reviews
* Growth opportunity into senior operations leadership as portfolio expands


If you have a proven track record in short-term rental operations and understand what it takes to consistently deliver luxury-level 5-star experiences while protecting revenue, we would love to hear from you.

Please submit your resume along with a brief summary of why you think you're a great fit for the role.