STR Guest Experience & Listing Optimization Specialist

Host with Wander is seeking an experienced short-term rental professional to manage guest communication and actively improve the performance of our luxury vacation-rental listings.

This is not simply a listing-creation or data-entry position. We need someone who understands how to optimize listings to increase search visibility, clicks, conversion, occupancy, and bookings.

Schedule

• 45 hours per week
• Five working days with two consecutive days off
• Some Weekend and Holiday coverage may be required
• The final schedule will be discussed with the selected candidate
• Must be fully available and dedicated to Host with Wander during scheduled hours

Primary Responsibilities

• Manage guest communication with warmth, professionalism, and urgency
• Resolve guest concerns and coordinate with cleaners and maintenance personnel
• Optimize listings across Airbnb, Vrbo, and our direct-booking website
• Improve listing titles, descriptions, amenities, photo order, captions, and positioning
• Research competing properties and identify opportunities for our listings to stand out
• Monitor listing performance and recommend measurable improvements
• Maintain accurate property information across Guesty and all booking channels
• Help launch and optimize new property listings
• Use ChatGPT and other approved tools to analyze performance and improve efficiency

Required Experience

• Hands-on short-term rental guest-communication experience
• Strong knowledge of Airbnb listing optimization
• Experience improving listings—not simply creating or uploading them
• Excellent written and spoken English
• Strong customer service and problem-solving abilities
• Ability to work independently and follow issues through completion
• Ability to review performance data and recommend improvements
• Willingness to learn and responsibly use AI tools

Experience using Guesty is a plus but is not required.

Complementary Specialty

In addition to guest communication and listing optimization, we would prefer someone with meaningful experience in at least one of the following areas:

Bookkeeping

• Organizing income and expense information
• Reviewing transactions and financial records
• Assisting with reconciliations or property-level reporting
• Experience with QuickBooks is a plus

Rankbreeze and Listing Analytics

• Tracking Airbnb search rankings
• Monitoring listing performance
• Conducting competitor research
• Using data to recommend and test listing improvements

Canva and Marketing Support

• Creating professional social media graphics
• Designing property guides, signs, or marketing materials
• Following an established brand style
• Editing templates and preparing polished visual content

Candidates do not need experience in all three areas. Please tell us which area is your strongest and provide specific examples of your work.

Team and Culture Expectations

Host with Wander is building a supportive and collaborative team. We want people who help one another, communicate openly, share information, and work together to solve problems.

The right candidate must:

• Be a genuine team player
• Communicate respectfully and professionally
• Be willing to assist teammates when support is needed
• Share important information rather than working in isolation
• Accept feedback positively and offer feedback constructively
• Take ownership and focus on solutions when problems occur
• Contribute to a culture where everyone works toward shared goals
• Care deeply about providing an excellent experience for every guest

Individual performance matters, but so does the success of the entire team.

Important

We are not looking for someone who has only uploaded or created Airbnb listings. You should understand what helps a listing rank and convert—and be able to explain how your previous work improved performance.

How to Apply

Begin your application with the words “Top Listing.”

Please include:

1. How many short-term rental properties you have supported.
2. Which property management systems and booking platforms you have used.
3. A specific listing you optimized, what you changed, and why.
4. Any measurable before-and-after results, such as ranking, conversion, occupancy, bookings, or revenue.
5. An example of a difficult guest situation you handled.
6. An example of how you supported or collaborated with a teammate.
7. Which complementary specialty is your strongest: bookkeeping, Rankbreeze/listing analytics, or Canva.
8. Specific examples of your work in that specialty.
9. How you currently use ChatGPT or other AI tools.
10. Confirmation that you can work 45 hours per week, including required weekend coverage.
11. Your requested hourly rate.

Please attach or link to listings you personally optimized. If Canva is your specialty, include a portfolio or work samples. If bookkeeping or Rankbreeze is your specialty, the tasks you personally handled and the results you achieved.