Guest Experience & Reservations Manager

Employment Type: Full-time, Independent Contractor

Work Model: Remote (United States)

Work Hours: US Eastern Standard Time (EST) alignment

Role Overview

We are seeking a hands-on, highly engaging Guest Experience & Reservations Manager to lead from the front, overseeing the full reservations pipeline and guest journey across our curated collection of luxury boutique properties.

This is not a "manage from above" seat—you will actively work alongside your team to set the bar for exceptional service. You will take inquiries, step into coverage during peak windows, coach in real time, and drive conversion metrics while ensuring every guest feels genuinely cared for rather than transactional.

Vacation rental management is a must.

Key Responsibilities

1. Guest Experience & Reservations Leadership

End-to-End Guest Journey: Own the complete guest lifecycle from initial inquiry through post-stay follow-up, identifying operational gaps and implementing continuous service improvements.
Team Development & Accountability: Hire, onboard, train, and coach a high-performing reservations team—setting clear expectations, providing real-time feedback, and fostering a culture of urgency, ownership, and detail.
Hands-On Coverage: Step into active shifts during peak demand periods, staffing gaps, or complex calls, leading by example in tone, responsiveness, and resolution quality.

2. Performance & Conversion Optimization

Pipeline Management: Oversee the entire reservations pipeline (inquiries, follow-ups, conversions, and finalized bookings), ensuring strict adherence to response-time standards.
KPI Execution: Track and optimize core performance metrics, including lead-to-booking conversion rates, response times, average booking value, and guest satisfaction (CSAT) scores.
Revenue Collaboration: Partner with executive leadership to align guest conversion tactics with broader demand generation and revenue management strategies.

3. Operational Excellence & Systems Hygiene

CRM & Data Hygiene: Maintain absolute data integrity within the CRM and reservations systems—tracking lead statuses, interaction notes, follow-up schedules, and attribution sources.
SOP Refinement: Develop and refine Standard Operating Procedures (SOPs) for reservations, guest communication, and issue escalations across phone, SMS, and email channels.

Required Skills & Qualifications

Hospitality Background: 5+ years of experience in hospitality, guest services, or reservations (vacation rental management or luxury boutique hospitality).
Leadership Track Record: 3+ years of proven experience managing, coaching, and developing direct reports with a leadership style rooted in accountability and active support.
Systems Literacy: Direct experience managing CRM platforms, reservations pipelines, and PMS/channel management software.
Executive Presence & Communication: Exceptional written, verbal, and guest-facing communication skills with a proven ability to perform under pressure in fast-paced environments.
Hands-On Operating Style: Equal comfort handling direct guest inquiries, de-escalating issues, and reviewing high-level conversion metrics.

Success Metrics (KPIs)

Conversion Rate Elevation: Driving higher lead-to-booking conversion rates across all inbound channels.
Response Velocity: Achieving faster response times and 100% follow-up consistency across inquiries.
Issue & Cancellation Reduction: Decreasing guest cancellations and refund requests through proactive communication and proper expectation setting.
Team Throughput: Developing an accountable reservations team that operates independently while continuously improving service quality.

Guest Experience & Reservations Manager - 20852