Job Description

Group Sales Supervisor

Position: Group Sales Supervisor

Area: Groups

Reports to: Director, Groups

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

The Group Sales Supervisor plays a pivotal role in turning group travel opportunities into exceptional experiences and meaningful revenue for Classic Vacations. Responsible for supporting the front end of the group sales journey, 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.

This is more than a traditional group sales role. The Group Sales Supervisor combines consultative selling, relationship management, negotiation, operational discipline, and team leadership to create a seamless experience for Travel Advisors, agency partners, and their clients. From destination weddings and room blocks to other group travel opportunities, this role helps clients navigate important decisions while keeping each opportunity moving confidently toward conversion.

As a supervisor, this position also helps create clarity and accountability within the Groups team. By reinforcing sales standards, supporting colleagues, identifying process improvements, and collaborating closely with Group Management and Group Coordinators, the Group Sales Supervisor helps ensure the team operates cohesively, efficiently, and with a shared commitment to exceptional results.

Why This Role Matters

Group travel represents some of the most meaningful and memorable experiences our clients will ever plan. Weddings, celebrations, milestone trips, and shared adventures bring together multiple travelers, competing priorities, detailed negotiations, and significant expectations. The Group Sales Supervisor helps transform that complexity into confidence.

This role matters because the earliest stages of a group opportunity often determine whether we earn the business and establish the trust necessary for a successful long-term relationship. Through thoughtful qualification, strong follow-up, compelling presentations, skilled negotiation, and genuine partnership, the Group Sales Supervisor helps turn interest into commitment while ensuring advisors and clients feel supported throughout the sales process.

The role also strengthens the health and performance of the broader Groups organization. Clear communication, accurate documentation, disciplined handoffs, and shared accountability create an environment where Sales and Group Coordination can operate as one cohesive team. By ensuring that contracted business is accurate, complete, and positioned for successful fulfillment, this role creates a stronger experience for everyone who touches the booking.

When we make complex group travel feel effortless, our advisors gain confidence, our clients feel cared for, and Classic earns relationships that extend far beyond a single booking.

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:

Group Sales & Conversion

Lead Qualification & Conversion: 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.
Consultative Selling: Understand each client's objectives, preferences, budget, and group requirements to recommend solutions that create value and support successful conversion.
Presentations & Proposals: Prepare compelling, accurate, and professional client presentations and proposals that showcase relevant travel options and clearly communicate the value of booking with Classic Vacations.
Weddings & Room Blocks: Assist Travel Advisors and clients with destination wedding packages, hotel room blocks, and other group travel needs, providing knowledgeable guidance throughout the sales process.

Negotiation & Contract Management

Proposal & Contract Negotiation: Partner with Group Management on proposal and contract negotiations, ensuring terms, expectations, and commitments are clearly communicated and appropriately documented.
Supplier Coordination: Support negotiations and communications involving hotels and other travel partners as appropriate to secure solutions that meet client needs and business objectives.
Sales Lifecycle Ownership: Maintain responsibility for client correspondence and follow-through from initial qualification through signed contract and receipt of the required deposit.
Seamless Handoff: 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.

Agency & Client Relationship Management

Agency Partnership: Build strong relationships with agency owners, Travel Advisors, and key account stakeholders to support mutual growth, trust, and long-term success.
Client Experience: Deliver responsive, knowledgeable, and high-touch service throughout the sales process with a strong commitment to client satisfaction.
Relationship Stewardship: Communicate proactively, manage expectations effectively, and ensure clients and advisors remain informed throughout the group sales journey.
Core Account Support: Provide dedicated sales and relationship support for assigned agency accounts and strategic business opportunities as directed.

Sales Operations & Data Accuracy

System Management: Accurately enter and maintain group booking information within designated group management systems, CRM platforms, and other applicable business tools.
Booking Accuracy: Strive for exceptional accuracy across group bookings, proposals, contracts, client correspondence, and related sales responsibilities.
Issue Identification: Recognize system discrepancies, booking inconsistencies, or process gaps and proactively recommend practical solutions.
Follow-Through: Maintain strong organization, time management, and follow-up practices to ensure deadlines, client commitments, and internal requirements are consistently met.

Supervisory Leadership & Team Collaboration

Team Support: Provide day-to-day guidance, support, and sales expertise to team members while reinforcing department standards and expectations.
Performance Accountability: Help foster an environment of ownership, follow-through, accuracy, and shared accountability for department goals.
Cross-Functional Partnership: 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.
Positive Team Culture: Demonstrate a strong work ethic, constructive attitude, and commitment to building productive relationships with colleagues, leadership, and cross-functional partners.

Process Improvement & Operational Excellence

Continuous Improvement: Identify opportunities to improve processes, streamline daily workloads, strengthen interdepartmental operations, and enhance internal and external communications.
Problem Solving: Approach challenges with curiosity and a solutions-oriented mindset, identifying root causes and recommending improvements that support efficiency and service.
Business Alignment: Prioritize work in support of departmental and company objectives while consistently meeting established deadlines.
Special Projects: Manage projects and additional initiatives as assigned by Group leadership in support of evolving business needs.

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, Hospitality, Travel & Tourism, Sales, Marketing, or a related field preferred. Equivalent relevant professional experience will also be considered.

Experience:

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.

Technical & Industry Expertise:

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.

Leadership & Professional Skills:

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.

Employment Terms & Benefits:

Hours: Full-time, salaried position with flexibility to meet business needs.
Office: Remote (USA).
Pay Rate: Competitive compensation based on experience.
Comprehensive benefits package: Including medical, dental, vision, 401(k) with company match, PTO, paid holidays, and exclusive travel industry perks.

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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