Director of Reservations

About the role

This is a hands-on hospitality leadership role with responsibility for a team of 20+ reservations agents and front desk staff. The role involves strengthening team performance, improving the guest experience, and building the systems and accountability needed to support a large and growing vacation rental portfolio.

Responsibilities

• Own the full employee lifecycle for the department, including hiring, onboarding, training, coaching, scheduling, performance management, and team development.
• Evaluate existing workflows, identify opportunities for automation and process improvement, and help build more scalable systems for a portfolio of 900+ vacation rentals.
• Lead reservations workflows and process development throughout the company's property management system transition.
• Partner with business leadership to translate departmental data into coaching priorities, staffing decisions, and operational improvements.

Requirements

• 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.
• 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.
• 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.

Qualifications

• Built training or QA programs from scratch.
• Homeowner communication experience, including owner referrals and owner stay changes.

Skills

• Strong interpersonal and communication skills.
• Ability to manage multiple tasks and prioritize effectively.
• Proficiency in reservation systems, property management software, CRM platforms, and other operational technology.

Benefits

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.

Pay

Competitive pay with growth opportunities & performance raises.

Schedule

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.