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