Director of Sales - Group Travel

Position Summary
Classic Escapes is seeking an experienced, highly motivated Director of Sales to lead and grow the company’s group travel sales. This role is responsible for originating new business, managing key accounts, and driving measurable revenue and passenger growth. The Director of Sales must work independently, proactively, and with minimal supervision, while maintaining consistent communication and accountability with management.

This position requires a strong hunter mentality, disciplined follow-through, and the ability to convert relationships into confirmed business.

Core Responsibilities

Business Development & New Accounts

• Actively prospect new organizations and affinity groups to generate new business.
• Maintain a consistent outreach program using phone, Zoom, email, LinkedIn, and in-person meetings.
• Identify, qualify, and cultivate new accounts that align with Classic Escapes’ group travel offerings.
• Expand the company’s portfolio of clients across universities, museums, associations, alumni groups, and affinity organizations.
• Maintain a steady pipeline of new prospects and opportunities.

Account Management & Relationship Building

• Establish and maintain productive, professional relationships with assigned accounts.
• Conduct regular outreach and follow-up to ensure continuity and momentum.
• Reactivate dormant or inactive accounts where appropriate.
• Represent Classic Escapes as a trusted partner and brand ambassador.

Sales Activity & Performance

• Conduct a consistent program of outbound sales activity, including prospecting and follow-up.
• Schedule and lead introductory and follow-up sales meetings.
• Support the sales process by coordinating internally to ensure proposals and materials are delivered accurately and on time.
• Present proposals and programs to clients and manage post-proposal follow-up.

Reporting & Visibility

• Maintain clear, up-to-date records of sales activity, leads, meetings, and account status (manual system or CRM, as applicable).
• Submit required weekly and monthly sales activity and pipeline reports.
• Provide management with accurate forecasts and visibility into the sales pipeline.

Strategic Contribution

• Provide market intelligence and insights on trends, competitors, and emerging opportunities.
• Collaborate with management on annual sales and growth strategies.
• Contribute ideas for expanding Classic Escapes’ reach into new markets and affinity segments.

Events & Industry Engagement

• Represent Classic Escapes at industry events, conferences, and sales meetings.
• Prepare for and actively participate in trade shows (e.g., ETC), including appointment setting and follow-up.
• Participate in educational travel (FAM trips) as required to support sales efforts.

Performance Expectations

To be successful in this role, the Director of Sales must demonstrate:

• Consistent prospecting and outreach activity
• Measurable growth in leads, meetings, and new accounts
• Strong follow-through and responsiveness
• Clear documentation and reporting
• Ability to operate independently without repeated reminders

Performance will be evaluated based on measurable results, not effort alone.

Qualifications

• Proven sales experience in travel, hospitality, or a related industry.
• Demonstrated ability to originate and close new business.
• Strong interpersonal, communication, and relationship-building skills.
• Highly organized with strong follow-through.
• Comfortable working independently with minimal supervision.
• Willingness to invest time outside normal office hours when necessary to support sales efforts.

Additional Notes

• This job description is not intended to be exhaustive and may be adjusted as business needs evolve.
• Continued employment is contingent upon sustained performance and achievement of sales objectives.

Salary: Commensurate with experience and will include a package that is based on a base salary and commission. Please list your requirements.