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About the Role

The Group Sales Supervisor plays a pivotal role in turning group travel opportunities into exceptional experiences and meaningful revenue for Classic Vacations. This position oversees the progression of qualified group opportunities from initial inquiry through signed contract and deposit, ensuring each interaction reflects the responsiveness, expertise, and service excellence that define the Classic® difference. The role combines consultative selling, relationship management, negotiation, operational discipline, and team leadership to create a seamless experience for Travel Advisors, agency partners, and their clients.

Responsibilities

Engage, qualify, and advance group sales opportunities, including inquiries involving five or more rooms at a single hotel, with a focus on converting qualified leads into contracted business.
Understand each client's objectives, preferences, budget, and group requirements to recommend solutions that create value and support successful conversion.
Prepare compelling, accurate, and professional client presentations and proposals that showcase relevant travel options and clearly communicate the value of booking with Classic Vacations.
Assist Travel Advisors and clients with destination wedding packages, hotel room blocks, and other group travel needs, providing knowledgeable guidance throughout the sales process.
Partner with Group Management on proposal and contract negotiations, ensuring terms, expectations, and commitments are clearly communicated and appropriately documented.
Support negotiations and communications involving hotels and other travel partners as appropriate to secure solutions that meet client needs and business objectives.
Maintain responsibility for client correspondence and follow-through from initial qualification through signed contract and receipt of the required deposit.
Ensure each contracted group is accurately and thoroughly transitioned to the Group Coordinator once the contract is signed and the required deposit has been received.
Build strong relationships with agency owners, Travel Advisors, and key account stakeholders to support mutual growth, trust, and long-term success.
Deliver responsive, knowledgeable, and high-touch service throughout the sales process with a strong commitment to client satisfaction.
Communicate proactively, manage expectations effectively, and ensure clients and advisors remain informed throughout the group sales journey.
Provide dedicated sales and relationship support for assigned agency accounts and strategic business opportunities as directed.
Accurately enter and maintain group booking information within designated group management systems, CRM platforms, and other applicable business tools.
Strive for exceptional accuracy across group bookings, proposals, contracts, client correspondence, and related sales responsibilities.
Recognize system discrepancies, booking inconsistencies, or process gaps and proactively recommend practical solutions.
Maintain strong organization, time management, and follow-up practices to ensure deadlines, client commitments, and internal requirements are consistently met.
Provide day-to-day guidance, support, and sales expertise to team members while reinforcing department standards and expectations.
Help foster an environment of ownership, follow-through, accuracy, and shared accountability for department goals.
Collaborate closely with the Director, Groups, Group Coordinators, Reservations, and other cross-functional partners to ensure smooth communication and execution throughout the group booking lifecycle.
Demonstrate a strong work ethic, constructive attitude, and commitment to building productive relationships with colleagues, leadership, and cross-functional partners.
Identify opportunities to improve processes, streamline daily workloads, strengthen interdepartmental operations, and enhance internal and external communications.
Approach challenges with curiosity and a solutions-oriented mindset, identifying root causes and recommending improvements that support efficiency and service.
Prioritize work in support of departmental and company objectives while consistently meeting established deadlines.
Manage projects and additional initiatives as assigned by Group leadership in support of evolving business needs.

Requirements

Minimum of 3 years of related experience in sales, travel, group travel, hospitality, or a comparable customer-facing environment.
Demonstrated experience qualifying opportunities, managing a sales pipeline, and successfully moving prospective business through the sales cycle.
Experience supporting group travel, hotel room blocks, destination weddings, or other complex travel arrangements strongly preferred.
Experience negotiating with hotels, airlines, or other travel suppliers preferred.
Prior experience providing team leadership, coaching, training, or supervisory support preferred.
Strong understanding of consultative sales, client relationship management, negotiation, and follow-up practices.
Proficiency with Microsoft Excel, Word, Outlook, internet-based tools, and business productivity applications.
Experience working with CRM, group management, reservation, or similar sales and booking systems preferred.
Ability to maintain accurate booking and client information across multiple systems and workflows.
Strong attention to detail with the ability to identify discrepancies and proactively recommend solutions.
Strong negotiation and influencing skills, particularly when working with businesses, suppliers, agency partners, and clients.
Excellent written and verbal communication skills with the ability to communicate confidently and professionally with a variety of audiences.
Strong time management, organization, and follow-up skills with the ability to manage multiple group opportunities and priorities simultaneously.
Service-oriented mindset with a strong commitment to advisor and client satisfaction.
Collaborative leadership style with the ability to build positive relationships across teams and departments.
Strong work ethic, sound judgment, and a high level of personal accountability.
Solutions-oriented mindset with a commitment to continuous improvement and operational efficiency.
Ability to remain adaptable, composed, and responsive in a fast-paced environment where priorities and client needs may evolve quickly.
Ability to perform essential job functions while working at a computer for extended periods.

Skills

Consultative Selling
Relationship Management
Negotiation
Operational Discipline
Team Leadership
Sales
Travel
Group Travel
Hospitality
Customer-facing
Pipeline Management
Sales Cycle Management
Hotel Room Blocks
Destination Weddings
Complex Travel Arrangements
Supplier Negotiation
Team Coaching
Team Training
Supervisory Support
Microsoft Excel
Microsoft Word
Microsoft Outlook
CRM Systems
Group Management Systems
Reservation Systems
Attention to Detail
Influencing Skills
Written Communication
Verbal Communication
Time Management
Organization
Follow-up
Service Orientation
Collaboration
Work Ethic
Judgment
Accountability
Problem Solving
Adaptability
Composure
Responsiveness

Location

Remote (USA)

Work Type

Remote
Full-time
Salaried

Experience Level

3 years of related experience
Supervisory experience preferred

Education Level

Bachelor's degree in Business, Hospitality, Travel & Tourism, Sales, Marketing, or a related field preferred.
Equivalent relevant professional experience will also be considered.

Salary/Compensations

Competitive compensation based on experience.

Benefits

Medical
Dental
Vision
401(k) with company match
PTO
Paid holidays
Exclusive travel industry perks

About the Company

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.
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.
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.

Equal Opportunity

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.
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.