Complex Reservations Manager

Highgate Hotels, LP; Key West (FL); On-site; USD 65,000 - 90,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

Disability insurance

401(k) with employer match

Paid holidays

Paid vacation

Paid sick leave

EAP

Tuition reimbursement

Jury duty leave

Job summary

Highgate Hotels, LP is seeking a Complex Reservations Manager in Key West, FL. You will oversee the Reservations Department, lead and coach agents, and collaborate with Revenue Management to maximize occupancy and revenue.

The role requires a strong background in hotel reservations, Opera PMS expertise, and a proven track record of team leadership in a fast-paced environment.

Qualifications

• High school diploma or equivalent required; Associate's or Bachelor's degree in Hospitality, Business, or a related field preferred.
• Minimum 3–5 years of hotel or resort reservations experience.
• Supervisory or management experience required.
• Strong knowledge of Opera PMS and booking channels.

Responsibilities

• Oversee the daily operations of the Reservations Department.
• Lead, coach, and develop reservation agents to ensure high performance and guest service.
• Monitor reservations, occupancy, call conversion, and other key performance metrics.
• Partner with Revenue Management to maximize room revenue and optimize inventory.
• Review booking trends and implement strategies to improve sales and guest satisfaction.
• Manage reservation systems, rate codes, packages, and promotions.
• Handle escalated guest concerns and resolve complex reservation issues.
• Prepare reports and analyze departmental performance.
• Recruit, hire, train, and schedule reservations team members.
• Conduct performance evaluations and coaching sessions.
• Develop and maintain reservation procedures, scripts, and training materials.
• Collaborate with Front Office, Sales, Marketing, and Finance teams.

Skills

Leadership

Coaching

Data analysis

Communication

Organization

Multitasking

Education

High school diploma

Associate/Bachelor's degree preferred

Tools

Opera PMS

Booking channels

Job description

Complex Reservations Manager

Highgate is a leading real estate investment and hospitality management company with over $15 billion of assets under management and a global portfolio of more than 400 hotels spanning North America, Europe, the Caribbean, and Latin America. With a 30-year track record as an innovator in the hospitality industry, this forward‑thinking company provides expert guidance through all stages of the property cycle, from planning and development through recapitalization or disposition. Highgate continues to demonstrate success in developing a diverse portfolio of bespoke lifestyle hotel brands, legacy brands, and independent hotels and resorts, featuring contemporary programming and digital acumen. The company utilizes industry‑leading revenue management tools that efficiently identify and predict evolving market dynamics to drive outperformance and maximize asset value. With an executive team of seasoned hospitality leaders and corporate offices worldwide, Highgate is a trusted partner for top ownership groups and major hotel brands. www.highgate.com

Location

Located in historic Old Town, Southernmost Beach Resort expands over 6 acres on a serene part of the island with Atlantic Ocean front views, gorgeous Key West architecture, and all the amenities you desire in a beach resort. Just a short walk or bike ride from Key West's boutique shops, art galleries, eclectic restaurants, and non‑stop nightlife, the resort spans over two city blocks and offers guest rooms that are located within easy reach of both the beach and world‑famous Duval Street.

Overview

The Complex Reservations Manager supports the daily operation of the Reservations Department by assisting with team leadership, guest service, training, and reservation accuracy. This position works closely with the Reservations Manager, Revenue Management, Front Office, and Sales teams to maximize occupancy, revenue, and guest satisfaction while ensuring exceptional service standards are maintained. The resorts are Southernmost Beach Resort & The Marker Resort.

Responsibilities

Oversee the daily operations of the Reservations Department.

• Lead, coach, and develop reservation agents to ensure high performance and exceptional guest service.
• Monitor reservations, occupancy, call conversion, and other key performance metrics.
• Partner with Revenue Management to maximize room revenue and optimize inventory.
• Review booking trends and implement strategies to improve sales and guest satisfaction.
• Manage reservation systems, rate codes, packages, and promotional offers.
• Handle escalated guest concerns and resolve complex reservation issues.
• Ensure accuracy of reservations, billing, routing instructions, and guest information.
• Prepare reports and analyze departmental performance.
• Recruit, hire, train, and schedule reservations team members.
• Conduct performance evaluations, coaching sessions, and team meetings.
• Develop and maintain reservation procedures, scripts, and training materials.
• Collaborate with Front Office, Sales, Marketing, and Finance teams.
• Ensure compliance with company policies, standards, and procedures.
• Drive continuous improvements in service quality, efficiency, and revenue generation.

Qualifications

• High school diploma or equivalent required; Associate's or Bachelor's degree in Hospitality, Business, or a related field preferred.
• Minimum 3-5 years of hotel or resort reservations experience.
• Previous supervisory or management experience required.
• Strong knowledge of hotel reservation systems, property management systems Opera (PMS), and booking channels.
• Understanding of revenue management principles, inventory controls, and rate strategies.
• Excellent leadership, coaching, and team development skills.
• Strong communication and interpersonal skills.
• Ability to analyze reports, identify trends, and make data‑driven decisions.
• Strong organizational and time management skills with attention to detail.
• Proficiency in Microsoft Office, including Excel, Word, and Outlook.
• Ability to multitask and work effectively in a fast‑paced environment.
• Flexible schedule, including weekends, holidays, and peak business periods as needed.
• Commitment to providing exceptional guest service and maintaining professional standards.

Benefits

We are pleased to offer to our full‑time associates a comprehensive and competitive benefits package designed to support your health, well‑being, and financial future.

• Medical insurance, dental insurance, vision insurance, life insurance, short‑term and long‑term disability insurance 401(k) Retirement Plan with employer matching contributions
• Paid holidays
• Paid vacation
• Paid sick leave (provided in accordance with applicable law)
• Employee assistance program (EAP)
• Educational opportunities / Tuition reimbursement
• Paid jury duty leave, personal leave, medical leave, and military leave in accordance with applicable law

For Employees Based in Washington

• 8 paid holidays per year
• Up to 20 days of paid vacation per year, based on classification and length of service
• Paid Sick & Safe Time accrues at 1 hour for every 30 hours worked, with up to 72 hours of unused time carried over from one anniversary year to the next.

For Employees Based in Colorado

• 8 paid holidays per year; employees working in the City of Denver receive 64 hours of designated holiday time per calendar year
• Up to 20 days of paid vacation per year, based on classification and length of service
• 6 days or 48 hours of Paid Sick Leave per year, accrued at 1 hour for every 30 hours worked.

For Employees Based in California

• 8 paid holidays per year
• Up to 20 days of paid vacation per year, based on classification and length of service, capped at 1.5x annual accrual rate; non‑supervisory employees working in the City of Los Angeles accrue up to 22 days of Compensated Time Off, based on length of service capped at 192 hours of combined PST and CTO.
• Paid Sick Time accrues at 1 hour for every 30 hours worked, unused time is carried over from one anniversary year to the next up to a maximum of 80 hours; employees working in the City of Los Angeles are provided 40 hours of Paid Sick Time annually on their anniversary, unused time is not carried over from one anniversary year to the next.

Please note that certain benefits described above for associates in Washington, Colorado, and California may vary for associates covered by a Collective Bargaining Agreement ("CBA"). For such associates, eligibility for and the terms and conditions of benefits are governed by the applicable CBA and any applicable plan documents, and may differ from the benefits described above. In the event of any conflict or inconsistency, the terms of the applicable CBA and governing plan documents will control, as applicable.

The above-referenced benefits do not apply to part‑time positions

Posting Date

This job opening was posted on 9/28/26 and will remain open for at least 75 days.