Job Description

About Fieldtrip

Fieldtrip is a luxury hospitality company that’s committed to setting the standard for short term rental (AirBNB) experiences. Our growing portfolio of 100+ luxury homes combine the best aspects of a home with the brand promise of a high-end hotel. We are focused on delivering a seamless guest through strong team collaboration, clear processes, and consistent service standards.

About the Role

We’re looking for a hands-on Guest Experience Manager who leads from the front, not from behind a desk. This is a fully remote leadership role responsible for overseeing the full reservations pipeline and guest journey, while actively working alongside the team to deliver a high-touch, seamless experience.

This is not a “manage from above” role. You’ll be involved in the day-to-day; taking inquiries, stepping into shifts, coaching in real time, and setting the standard for what great service looks like.

What You’ll Do

Lead the Guest Experience Team

• Manage a team of 6 guest service associates, owning the end-to-end guest journey; from first inquiry to post-stay follow-up
• Ensure every interaction reflects a high-quality, personalized experience
• Identify gaps in our SOPs and implement improvements
• Handle high-stakes, sensitive guest resolutions cases 

Manage & Elevate the Reservations Team

• Hire, train, and develop a high-performing reservations team
• Set clear expectations and hold the team accountable to performance standards
• Coach in real time; providing feedback, improving communication quality, and closing gaps
• Build a culture of ownership, urgency, and attention to detail

Drive Performance

• Oversee reservations pipeline: inquiries, follow-ups, conversions, and bookings
• Ensure response time standards and follow-up cadences are consistently met
• Track and improve KPIs (conversion rate, response time, booking value, guest satisfaction)
• Balance guest experience with revenue outcomes in day-to-day decision-making
• Partner with leadership to align demand and conversion strategies

Be in the Work

• Step into shifts as needed; handling guest inquiries, calls, and bookings
• Support the team during peak periods, staffing gaps, or high-demand windows
• Lead by example in tone, responsiveness, and service quality

Operational Excellence

• Maintain CRM accuracy and pipeline integrity (lead status, notes, follow-ups, sources)
• Refine SOPs for reservations, communication, and guest experience
• Ensure consistency across all guest communications (email, SMS, phone)

What We’re Looking For

• 5+ years in hospitality, guest services, or reservations (vacation rentals or luxury hospitality preferred)
• 3+ years of proven experience managing and developing teams
• Strong leadership style rooted in accountability
• Comfortable being both strategic and highly hands-on
• Excellent communication skills; written, verbal, and guest-facing
• Experience with CRM systems and reservations pipelines
• Ability to negotiate and have difficult conversations with high-value guests

What Sets You Apart

• You have a proven track record dealing with difficult, high-stakes customers.
• You don’t just manage; you coach, fix, and improve in real time
• You don’t let things slip
• You’re just as comfortable taking a guest call as you are reviewing performance metrics
• You lead by doing and teaching, not delegating everything

Success in This Role Looks Like

• Faster response times and stronger follow-up consistency
• Increased lead-to-booking conversion rates
• Reduced cancellations and refunds through better guest alignment and communication
• A team that performs independently, but improves continuously
• Guests who feel taken care of, not processed

Benefits & Pay

• $70,000 - $85,000 depending on experience 
• Healthcare stipend
• Complimentary stays at Fieldtrip properties

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