Complex Reservations Supervisor

Compensation Type

Highgate Hotels

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 Reservations Supervisor is responsible for handling reservations, inquiries and cancellations in an attentive, courteous and efficient manner, and quoting available rates to maximize room revenue according to Highgate Hotel standards. He/she is also responsible for participating in the monthly Rooms Merchandising meeting.

Responsibilities

• Supervise and support the daily operations of the Reservations Department.
• Lead, coach, train, and develop reservation associates.
• Monitor call quality, email response times, and guest service standards.
• Ensure reservations are entered accurately and efficiently into the property management system.
• Assist guests with room reservations, modifications, cancellations, and special requests.
• Resolve guest concerns and escalated reservation issues in a professional and timely manner.
• Coordinate closely with Front Office, Revenue Management, Sales, and other departments to ensure seamless guest experiences.
• Monitor room inventory, occupancy levels, and booking trends.
• Assist with implementing rate strategies, promotions, and package offerings.
• Review daily, weekly, and monthly reservation reports.
• Maintain knowledge of hotel amenities, services, local attractions, and special events.
• Ensure compliance with company policies, brand standards, and reservation procedures.
• Assist with scheduling and staffing to ensure adequate department coverage.
• Perform additional duties as assigned.

Supervisory Responsibilities

• Directly supervise Reservation Agents.
• Conduct training, coaching, performance evaluations, and corrective action when necessary.
• Foster a positive, team-oriented work environment.

Qualifications

• • High school diploma or equivalent required; college degree preferred.
  • Minimum 2 years of hotel reservations experience required.
  • Prior supervisory experience preferred.
  • Knowledge of hotel property management systems and reservation software.
  • Strong customer service, communication, and problem-solving skills.
  • Ability to multitask and prioritize in a fast-paced environment.
  • Proficiency with Microsoft Office applications.
  • Ability to sit for extended periods while working on a computer.
  • Ability to communicate effectively by phone, email, and in person.

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 insurance401(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 9/28/2026 and will remain open for at least 75 days.