Group Sales Supervisor

Classic Vacations, LLC•Concord, NH

5d•$68,000 - $78,000•Remote

About The Position

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.

Requirements

Bachelor's degree in Business, Hospitality, Travel & Tourism, Sales, Marketing, or a related field preferred. Equivalent relevant professional experience will also be considered.
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.
Proficiency with Microsoft Excel, Word, Outlook, internet-based tools, and business productivity applications.
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.

Nice To Haves

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.
Experience working with CRM, group management, reservation, or similar sales and booking systems preferred.

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.