Guest Services / Customer Support

About the Role

Reports to: Founder

Our client is an established short-term rental property management company managing approximately 30 homes and 34 listings in its local market. The company has been in business for five years and handled thousands of bookings last year. With direct bookings increasing by approximately 30% year over year and continued investment in its website and guest experience, the business is continuing to grow.

We're looking for a Guest Services / Customer Support representative who can become a reliable extension of the team—an A-player who can take ownership of day-to-day guest communication, monitor incoming calls and messages, and help ensure operational issues are identified and addressed before they become larger problems.

This role is primarily focused on guest services and communication. You'll monitor the phones, Airbnb/VRBO messages, email , and Breezeway tasks, helping the team stay ahead of guest needs and operational issues. The goal is not simply to respond to messages, but to provide the kind of warm, natural, thoughtful communication that reflects the level of service our client wants its guests to receive.

The company has invested heavily in documenting its properties and building a centralized repository of property information, including videos, photos, appliance information, and other details. This gives the right person the resources needed to learn the homes and quickly find accurate answers rather than relying on the local team for every question.

The company is also incorporating AI into its guest communication workflows. The AI currently provides suggested responses that the team can review, approve, or revise. The Guest Services / Customer Support will bring the human judgment required to audit these responses, recognize when something doesn't sound right, and make sure communication remains natural and appropriate for the guest.

This is not a basic administrative VA role. We're looking for someone who understands short-term rental operations, communicates confidently with guests, and can use good judgment without needing constant direction. The ideal candidate will be comfortable stepping into a busy environment, learning the property portfolio, and becoming a dependable resource for the team.

As the business continues to grow, there is potential for this to become a long-term position with additional responsibilities and the opportunity to support the future Assistant Manager / Operations Manager.

What You’ll Own

Guest Services & Communication (Primary Focus)

• Guest Communication: Monitor and respond to guest inquiries through Airbnb/VRBO messaging, email , and other communication channels.

• Phone Coverage: Monitor incoming calls through RingCentral and confidently communicate with guests by phone.

• Responsiveness: Maintain a response time of approximately 20 minutes or less during assigned working hours.

• Guest Experience: Provide warm, natural, patient, and thoughtful communication rather than short or transactional responses.

• Problem Resolution: Use available property information and resources to answer guest questions and resolve routine issues independently.

• Escalation: Recognize situations that require the local team's attention and escalate appropriately, particularly when an issue is urgent or could impact the guest experience.

Breezeway & Property Operations Support

• Task Monitoring: Monitor Breezeway tasks alongside incoming guest communication and identify items that may require attention.

• Issue Identification: Review tasks and updates, recognize where there may be an operational issue, and flag it before it becomes a larger problem.

• Updates: Keep relevant information and task statuses updated in the appropriate systems.

• Property Knowledge: Become familiar with the company's homes, amenities, appliances, and property-specific information so that guest questions can be answered accurately.

AI & Technology Support

• AI Response Review: Review AI-generated guest responses and determine whether they are appropriate before they are sent.

• Human Judgment: Recognize when an AI response doesn't sound natural, has an issue with syntax, doesn't make sense, or fails to address the guest's actual situation.

• System Navigation: Work confidently across the company's technology platforms and quickly learn new tools.

• Knowledge Base: Use the Prohost Guidebook database and other internal resources to find the information needed to assist guests.

Administrative & Property Support

• Property Setup: Assist with property onboarding and setup tasks as needed, including uploading photos, descriptions, and other property information.

• Administrative Support: Assist with other recurring administrative or operational tasks when guest-service volume allows.

• Content Support: Support basic social media or other marketing-related tasks when appropriate.

• Documentation: Help keep property information and operational resources organized and up to date.

Who This Role Is For

You may be a strong fit if you:

• Have STR Experience: You understand short-term rental or vacation rental operations and the pace and expectations that come with guest stays.

• Are Guest-Focused: You genuinely care about providing an excellent guest experience and understand the importance of making guests feel heard and valued.

• Communicate Naturally: You have excellent spoken and written English and can communicate with guests in a warm, conversational, professional way.

• Are Comfortable on the Phone: Speaking with guests by phone is second nature to you. You can confidently answer questions, handle unexpected situations, and communicate professionally.

• Have Strong Judgment: You know when to handle an issue yourself, when to investigate further, and when something needs to be escalated.

• Operate with Urgency: You understand that guest communication and operational issues are time-sensitive and should not sit unattended.

• Are Proactive: You don't simply wait for someone to tell you what to do. You monitor what is happening, identify potential issues, and take appropriate action.

• Are Self-Directed: You can use available resources, search for answers, and work through problems independently rather than immediately relying on the founder or assistant manager.

• Are AI-Fluent: You are comfortable working with AI-assisted communication tools and understand that AI-generated responses still require human oversight and judgment.

• Learn Quickly: You can absorb property-specific information, systems, and processes without becoming overwhelmed.

• Have a Service Mindset: You understand that great guest communication requires empathy, patience, attention to detail, and good instincts—not simply following a script.

Preferred Qualifications

• Hands-on experience in short-term rental, vacation rental, hospitality, or property management.

• Previous experience handling guest communications for Airbnb, VRBO, or similar platforms.

• MUST have experience with RingCentral, Slack, Prohost, Sway, OwnerRez, Breezeway, and ClickUp.

• Experience working with AI-assisted customer service or guest communication tools.

• Experience supporting multiple properties or a property management portfolio.

• Experience with property onboarding or setup, including uploading photos, descriptions, and property information.

• Additional administrative, marketing, or social media experience is a plus.

Compensation & Schedule

• Hourly Rate: $6–10/hr, based on experience, with openness toward the higher end of the range given the company's immediate need.

• Priority Coverage: Wednesday–Saturday and Monday approximately 10am–7:00 PM Pacific Time, when guest activity and operational demands are particularly high.

• Availability: Saturday availability is important, with flexibility around the exact schedule based on business needs.

• Long-Term Opportunity: While the immediate need is to provide additional guest-service coverage, this is not intended to be a short-term gap-filler. If the right person is successful, there is potential for the role to continue long-term and provide support to the future Assistant Manager.

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