Classic Vacations Jobs (NOW HIRING)

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

Negotiation & Contract Management

Agency & Client Relationship Management

Sales Operations & Data Accuracy

Supervisory Leadership & Team Collaboration

Process Improvement & Operational Excellence

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:

Experience:

Technical & Industry Expertise:

Leadership & Professional Skills: