Director of Reservations

Company Overview

Panhandle Getaways is proud to be recognized as one of the Top 50 Vacation Rental Property Management Companies in the World by Rentals United. Managing over 900 short-term vacation rental properties along the Florida Panhandle, we deliver exceptional guest experiences while maintaining strong relationships with our homeowners.


Position Summary

Panhandle Getaways is seeking an experienced Director of Reservations to lead and elevate our reservations and front desk operations across four markets. This is a hands-on hospitality leadership role with responsibility for a team of 20+ reservations agents and front desk staff, with a clear mandate to strengthen team performance, improve the guest experience, and build the systems and accountability needed to support a large and growing vacation rental portfolio.

You will own the full employee lifecycle for the department, including hiring, onboarding, training, coaching, scheduling, performance management, and team development. Just as importantly, you will establish the standards behind every guest interaction by building stronger training, quality assurance, conversation tracking, KPIs, and reporting.

This role will also play a key leadership role in the reservations side of our upcoming property management system transition. You will evaluate existing workflows, identify opportunities for automation and process improvement, and help build more scalable systems for a portfolio of 900+ vacation rentals.

This is not a desk-only Director position. Initially, you should expect to spend significant time working alongside the team, including taking guest calls, observing workflows firsthand, coaching in real time, and identifying where processes are breaking down. As you strengthen the team, develop supervisor-level support, and improve departmental systems, your focus will increasingly shift toward leadership, performance management, training, and strategic improvement.

You will work closely with our Director of Guest Services , who will be a key operational partner in team management, escalated guest situations, and day-to-day problem solving. Together, you will create a reservations operation that is responsive, accountable, data-driven, and consistently delivers an exceptional guest experience.

What You'll Own

• Lead, develop, and hold accountable a team of 20+ reservations agents and front desk staff across four markets (30A, Destin, Panama City Beach and the Forgotten Coast)
• Own departmental hiring, onboarding, training, coaching, performance reviews, employee development, and termination decisions
• Build and continuously improve the department's training curriculum, quality standards, and new hire ramp-up process
• Oversee scheduling, hourly payroll approvals, PTO and schedule changes, staffing coverage, and overtime management
• Establish a consistent quality assurance process for monitoring guest conversations, identifying coaching opportunities, and improving service standards
• Analyze guest reviews and feedback to identify root causes, recurring reservation issues, and opportunities for operational improvement
• Lead reservations workflows and process development throughout the company's property management system transition
• Identify and champion opportunities for automation, workflow improvement, and greater operational efficiency
• Build guest conversation tracking, departmental reporting, and performance visibility from the ground up
• Establish and report on key departmental metrics, including speed to answer, call abandonment, response times, booking conversion, guest satisfaction, new hire ramp time, and team performance
• Partner with business leadership to translate departmental data into coaching priorities, staffing decisions, and operational improvements
• Serve as the primary reservations liaison with housekeeping, maintenance, owner services, revenue management, and other operational teams

Required Qualifications

• 5+ years of experience in reservations, guest services, hospitality operations, or a related customer-facing environment, including at least 3 years in a people leadership role
• Proven experience leading, coaching, and holding accountable a team of 15+ employees in a fast-paced service environment
• Demonstrated ability to develop employees through structured onboarding, training, coaching, performance feedback, and accountability
• Experience using KPIs, reporting, and performance data to identify trends, coach employees, and improve departmental results
• Strong operational judgment with the ability to balance exceptional guest service, company policies, and sound business decisions
• Experience handling escalated guest situations and coaching others to confidently resolve challenging conversations
• Strong organizational and process management skills
• Comfortable learning and working within reservation systems, property management software, CRM platforms, and other operational technology
• Experience collaborating cross-functionally with departments such as housekeeping, maintenance, revenue management, owner services, or comparable operational teams
• Ability and willingness to work on-site five days per week and initially spend significant time working alongside the reservations team, including handling guest calls

Preferred Qualifications

• Built training or QA programs from scratch

• Homeowner communication experience, including owner referrals and owner stay changes

What's Great About Working with Us

• Stable, locally owned company with strong community roots and family operated

• Manage one of the largest vacation rental portfolios in the area (900+ homes)

• Competitive pay with growth opportunities & performance raises

• Full Benefits: Health with HSA, dental, disability, life and vision insurance

• Retirement account with generous ~4% company match
• Workplace perks such as recreation activities, food and coffee, and flexible work schedules

• A genuinely fun and supportive team that is constantly improving while celebrating the wins