Guest Experience Associate

COMPANY OVERVIEW:

Fieldtrip (@stayfieldtrip) is a luxury hospitality + real estate firm specializing in the acquisition, development, and management of premium branded short-term rentals. We aspire to be the leading boutique hospitality brand in the luxury short-term rental space, currently operating over $100M in assets, with an additional $50M+ in homes, boutique hotels, and glamping projects in development. Our collection includes the world-famous Invisible House, as well as one of the nation’s largest purpose-built short-term rental portfolios. We own or exclusively manage the assets in our portfolio, selectively partnering with family offices, investment firms, developers, and homeowners who share our vision and seek to be part of our curated collection.

Hospitality is at the core of what we do. Our properties are professionally designed to the Fieldtrip brand standard, allowing us to scale and operate our portfolio like a distributed full-service boutique hotel. At each destination, our professional local teams facilitate a seamless and unique experience for our discerning travelers by ensuring that our homes are in perfect condition and prepared for our guests’ specific needs. Our Experience Curation team, dedicated concierge, and 24/7 Guest Experience team provide prompt support and curate bespoke travel experiences and immersive activities. The quality of our white-glove service is evident in our 2000+ 5-star ratings.

POSITION SUMMARY:

We’re looking for an energetic, reliable, and experienced vacation rental guest experience/guest service associate who can join our remote team as a member of our Guest Experience department. Working under our Head of Guest Experience, you’ll be assigned to a shift working from 6 am to 3 pm Los Angeles time, five days a week. There are opportunities for working six days a week if desired.

During your shift, you will be responsible for performing various vacation rental guest experience tasks, including:

• guest communications
• reservation inquiries and bookings
• reservation folio audits
• guest concierge management
• resolutions case management
• and other guest experience-related administrative tasks.
  
  

Using a hotel analogy, this virtual assistant position is a combination of hotel front desk and reservationist with some elements of concierge and resolutions. The position requires meticulous attention to detail, excellent written and verbal English communication, superior organizational skills, and unparalleled calmness, politeness, and caring.

The position will involve heavy use and administration of the Streamline property management system, Slack, Breezeway task management platform, Front communications platform, and Monday.com. We need a self-starter who sets an example of work agility and productivity while being obsessed with high-quality guest service. You must be capable of learning quickly and comfortable jumping right in.

After a week of indoctrination training, the remainder of our training will be On-the-Job (OJT) based. If you are timid or prefer slow-paced work, please dont apply. We are a fast-paced, growing company, and we need production from every member of the team.

There is a lot of opportunity for growth and we frequently promote within. Competitive comp packages and benefits are included for the right candidate.

RESPONSIBILITIES:

• Respond to guest reservation inquiries via email, text, and phone through the Front communications platform, meeting our Service Level Agreements (SLAs).
• Interact with booked guests prior to, during, and immediately following their stay to answer their questions (usually by text or email, but sometimes via phone).
• Coordination with local market field operations managers for in-stay guest inquiries or issues.
• Assist with resolution and guest damage cases.
• Assist in creating and maintaining accurate property listings on all Online Travel Agencies (OTAs).
• Track and update our property and guest tasks in Monday.com and Breezeway.
• Assist with guest concierge requests or perform online research to answer guests questions regarding local recommendations or services.
• Do whatever it takes to ensure a 5-star guest experience!
  
  

QUALIFICATIONS:

• Must have excellent English skills, both written and verbal.
• Must have at least 3 (preferably 5+) years of experience working in the short-term rental space doing both guest experience and administrative work.
• Must have experience working with a US, Canadian, Australian, or UK-based employer.
• Previous management experience is strongly preferred. We are looking to grow future managers.
• Experience with Streamline Property Software is strongly preferred.
• Experience with Airbnb, HomeAway/VRBO is strongly preferred.
• Experience with Google Suite, Monday.com, and Slack is highly preferred.
• Experience with Breezeway software platform is a plus.
  
  

COMPENSATION & BENEFITS:

Monthly Salary: $800-1000

Bonus Details: 13th month bonus

Benefits:

• Paid time off, such as PTO, sick days, and vacation days
• Health insurance
  
  

IMPORTANT:

Please read the instructions carefully before applying.

This role requires strong attention to detail—and that begins with how you apply.

To be considered, all required materials must be submitted in full at the time of application.

Incomplete submissions will not be reviewed.

If you’re not yet ready to submit all items, we kindly ask that you wait until you are.

This ensures fairness and helps us keep the process efficient for everyone.

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