What are the responsibilities and job description for the Supervisor, Reservations position at Classic Vacations, LLC?
Job Description
Supervisor, Reservations
Position: Supervisor, Reservations
Area: Call Center
Reports to: Director of Reservations, ADS
Location: Remote
Target Start: ASAP
About Classic Vacations – The Classic® Difference
Classic Vacations is the #1 luxury vacation wholesaler for Travel Advisors, driven by a singular purpose: to delight our clients
with exceptional vacation experiences. Our team’s commitment to excellence ensures that every journey we create is
seamless, luxurious, and filled with unforgettable moments. We take pride in our role as trusted partners to travel
professionals worldwide, providing world-class accommodations, unparalleled service, and exclusive privileges in premier
destinations.
Role Overview
At Classic Vacations, we don’t just book trips — we help create lifelong memories through extraordinary travel experiences. As Supervisor, Reservations, you will lead a dynamic team of Travel Sales Specialists who bring those dreams to life for travelers and Travel Advisors around the world.
In this role, you’ll be responsible for driving sales excellence, fostering team development, and ensuring every client interaction reflects The Classic Difference — our unwavering commitment to exceptional service, product expertise, and care. You’ll guide your team toward achieving performance goals, building confidence and enthusiasm, and consistently delivering the high standards that define Classic Vacations.
If you’re a natural leader who thrives in a fast-paced, service-driven environment — one who finds joy in developing others and takes pride in creating seamless customer experiences — this is the perfect opportunity to make an impact in luxury travel.
Why This Role Matters
For more than 45 years, Classic Vacations has been the trusted partner of Travel Advisors, curating luxury travel experiences that exceed expectations. The Supervisor, Reservations plays a vital role in upholding that legacy — leading the talented Travel Sales Specialist team that transforms inquiries into unforgettable journeys.
This position is about more than managing daily operations — it’s about inspiring people. As a leader, you’ll cultivate a culture of excellence, empowering your team to deliver world-class service while fostering collaboration, accountability, and pride in every interaction. Your ability to coach, motivate, and develop others ensures that each traveler feels cared for and every Travel Advisor feels supported.
At Classic Vacations, leadership means leading with heart, purpose, and professionalism. You’ll help your team embody The Classic Difference — a dedication to quality, integrity, and extraordinary experiences — while driving performance and upholding our reputation as the premier name in luxury travel. This your opportunity to lead with purpose and passion.
Key Responsibilities
Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.
In alignment with Classic’s commitment to building a cohesive and high-performing team, your responsibilities will include:
Team Leadership & Motivation
- Lead, coach, and inspire a team of Travel Sales Specialists to meet and exceed performance goals.
- Foster a positive, collaborative, and energetic work environment that encourages engagement and accountability.
- Promote team morale and connection through motivation, recognition, and employee engagement activities.
Training & Development
- Partner with the Training Team to develop and implement effective skill-building programs.
- Provide regular coaching on sales techniques, customer communication, and product expertise.
- Encourage professional growth by fostering a culture of continuous learning and development.
Performance Management
- Monitor team metrics, KPIs, and service level goals to ensure operational excellence.
- Conduct monthly one-on-one meetings and performance reviews, providing clear feedback and action plans.
- Administer Performance Improvement Plans (PIPs) and corrective actions when necessary to support team success.
Customer Experience & Relationship Building
- Ensure every customer interaction reflects Classic’s commitment to world-class service.
- Build and maintain strong relationships with Travel Advisors to promote trust and collaboration.
- Partner with Customer Care, Operations, and Product teams to quickly resolve complex or escalated issues.
Inbox & Workflow Oversight
- Supervise the management of department inboxes (CV4U, EU4U, and others) to ensure timely, accurate, and professional responses.
- Prioritize workloads, monitor response times, and support team members in delivering exceptional service.
- Address escalations promptly, modeling calm and solution-oriented leadership.
Data Analysis & Reporting
- Analyze daily and monthly performance reports to identify opportunities for improvement.
- Lead regular team meetings to review metrics, share insights, and align on business priorities.
- Use data to drive decision-making, efficiency, and service improvements.
Cross-Functional Collaboration
- Partner with Outside Sales and Business Development teams to align on Advisor support and client engagement.
- Collaborate with Product, Operations, and Customer Service teams to communicate feedback and streamline workflows.
- Serve as a liaison between internal departments to ensure consistency and coordination across functions.
Operational Excellence
- Maintain expertise in Classic Vacations’ systems, policies, and product offerings.
- Promote adherence to processes while driving continuous improvement and innovation.
- Lead by example with professionalism, integrity, and a passion for excellence in every interaction.
The above is intended to describe the general content of and requirements for the performance of this position. It should
not be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job
description restricts management’s right to assign or reassign duties and responsibilities to this position at any time.
Qualifications & Skills
In line with Classic’s values of continuous improvement and organizational health, we seek a leader who exemplifies both
technical expertise and a collaborative spirit.
Education:
- Bachelor’s degree in Business Administration, Hospitality Management, or a related field preferred.
Experience:
- Minimum of 3 years in a supervisory or leadership role within reservations, contact center, or hospitality operations.
- Proven experience leading high-performing teams in sales and customer service environments.
- Demonstrated ability to achieve or exceed performance, quality, and customer satisfaction goals.
Skills:
- Proficiency in sales strategies, performance management, and customer service best practices.
- Strong analytical and reporting skills with the ability to interpret data and implement action plans.
- Excellent communication and interpersonal skills with the ability to influence and inspire others.
- Advanced computer proficiency in Microsoft Office Suite (Excel, Outlook, Word, PowerPoint).
- Experience with Plex or similar reservation/CRM systems preferred; Smartsheet knowledge is a plus.
Competencies:
- Inspiring leader with a passion for coaching and developing others.
- Results-oriented mindset with the ability to thrive under pressure.
- Strong organizational and time-management skills, balancing multiple priorities effectively.
- Collaborative, empathetic, and adaptable, with a commitment to service excellence.
- Genuine enthusiasm for travel, learning, and helping others succeed.
Employment Terms & Benefits:
- Hours: Full-time, 40 hours per week with flexibility to meet business needs.
- Location: Remote (USA).
- Compensation: Competitive salary commensurate with experience performance-based incentives.
- Benefits Package:
Medical, Dental, and Vision insurance
401(k) with company match
Life Insurance, Long-Term Disability, and Short-Term Disability
Paid holidays and generous PTO
Exclusive travel perks and industry discounts
Physical Requirements:
- Ability to perform essential job functions while working at a computer for extended periods.
At Classic Vacations, we’re more than a travel company—we’re dream makers. Our team is passionate, driven, and committed to delivering world-class service while fostering a culture of collaboration, innovation, and excellence.
By joining us, you’ll be part of a company that values its people, prioritizes work-life balance, and provides opportunities for personal and professional growth. Together, we’ll redefine luxury travel experiences and make lasting impacts on clients’ lives.
Entrepreneurial Mindset and Adaptability
In our entrepreneurial and collaborative environment, every team member is encouraged to contribute to the ongoing improvement and success of the organization. While each role has specific responsibilities, we embrace flexibility,
and salaried employees may engage in tasks beyond the traditional job scope when these opportunities arise. This approach fosters professional growth, allowing individuals to expand their skills, take on new challenges, and build strong cross-departmental relationships. Aligned with our commitment to mutual success, team innovation, and shared accountability, we believe that empowering every employee to actively participate in organizational growth enhances both individual development and our ability to serve our customers and community.
Classic Vacations’ Commitment to Diversity & Inclusion
Classic Vacations is an Equal Opportunity Employer. We are dedicated to fostering an inclusive workplace where every team member is valued, respected, and supported, regardless of background. We are committed to a culture
that celebrates diversity and empowers all employees to reach their full potential.
Affirmative Action Statement
It is the policy of Classic Vacations to provide equal employment opportunities without regard to race, color, religion, sex, national origin, age, disability, marital status, veteran status, sexual orientation, genetic information, or any other protected characteristic under applicable law. This policy relates to all phases of employment, including, but not limited to, recruiting, employment, placement, promotion, transfer, demotion, reduction of workforce and termination, rates of pay, and all other conditions and terms of employment. EEOE/M/F/Vet/Disabled. All your information will be kept confidential according to EEO guidelines.
For more information, please contact Classic Vacations Human Resources @ questions@classicvacations.com
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