JOB DESCRIPTION

POSITION:                 Senior Director of Sales

FLSA:                         Exempt

DEPARTMENT:          Sales & Conference Services 

REPORTS TO:           General Manager

SUMMARY: The Senior Director of Sales is responsible for motivating, leading, and developing the resort’s sales team while also contributing directly to sales growth. This role balances leadership with hands-on selling, coaching team members throughout the sales cycle, demonstrating best-in-class practices, and actively pursuing new business opportunities. The role holds strategic importance to Wintergreen’s continued growth and success as a year-round destination. 

The Senior Director ensures the sales team is engaged, focused, and accountable while personally maintaining a portfolio of accounts and contributing to overall group revenue growth across weddings, conferences, corporate meetings, banquets, and leisure groups. Success requires a dynamic leader who can inspire others, build strong client relationships, and consistently generate new business for the resort.

PRIMARY RESPONSIBILITIES:

Leadership & Team Development

• Lead, motivate, and inspire the sales team to achieve and exceed revenue targets, instilling a culture of accountability, professionalism, and service excellence.
• Provide consistent coaching, mentoring, and support by joining team members on client calls, site visits, and presentations.
• Conduct regular performance reviews, establish clear sales goals, and implement incentive programs to drive engagement and results.
• Recruit, train, and onboard new sales team members, ensuring they are equipped with the tools and knowledge to succeed.
• Promote a culture of continuous learning through regular training, industry education, and performance feedback.

Active Sales & Business Development

• Personally generate sales through prospecting, relationship-building, and account management of key market segments including weddings, conferences, corporate retreats, association meetings, and social events.
• Lead key sales presentations, proposals, and negotiations, modeling best practices for the team.
• Maintain a personal portfolio of accounts, balancing leadership duties with individual contribution to overall revenue goals.
• Actively pursue new business opportunities by attending trade shows, networking events, and industry functions.
• Ensure consistent lead follow-up and pipeline nurturing through CRM best practices.

Client & Partner Relationships

• Build strong, long-term relationships with high-value clients, event planners, and industry partners to drive repeat business and referrals.
• Serve as an escalation point for key clients, ensuring concerns are resolved quickly and effectively.
• Collaborate with catering, conference services, and operations teams to deliver on client expectations and ensure smooth handoffs from sales to execution.
• Represent the resort as a brand ambassador in the marketplace, reinforcing its reputation for excellence.

Sales Strategy & Reporting

• Develop and execute comprehensive sales strategies that align with the resort’s revenue goals and market positioning.
• Monitor market trends, competitor activity, and client demand patterns to adjust sales tactics proactively.
• Oversee accurate forecasting, pipeline management, and regular reporting to senior leadership, providing insights and recommendations for growth.
• Create and manage the departmental budget, including payroll, trade show expenses, travel, and association memberships.
• Leverage data analytics and historical performance metrics to inform strategy and optimize conversion rates. 

Cross-Department Collaboration

• Partner with Marketing to design targeted campaigns, sales collateral, and digital strategies that support group sales objectives.
• Collaborate closely with Lodging, Food & Beverage, and Operations to ensure group commitments are executed seamlessly and profitably.
• Participate actively in resort leadership meetings, contributing to broader business strategies and long-term growth planning.
• Communicate sales performance, opportunities, and departmental updates to leadership and cross-functional teams to maintain alignment.

MINIMUM QUALIFICATIONS:

• Strong administrative and computer skills, with proficiency in Microsoft Office Suite and CRM software.
• Highly organized with the ability to manage multiple tasks, deadlines, and priorities in a fast-paced environment.
• Self-motivated and capable of working independently, while also effectively supervising sales team and support staff when applicable.
• Able to remain calm and focused under pressure, especially when handling multiple high-priority projects.
• Detail-oriented with excellent time management and inventory tracking skills.
• Professional, friendly, and client-focused demeanor with a commitment to exceptional service.
• Strong interpersonal and communication skills, with the ability to work well with clients, colleagues, and external partners.

EDUCATION, TRAINING AND EXPERIENCE GUIDELINES:

• Bachelor's degree in Business, Hospitality Management, or related field preferred. Equivalent professional experience in group sales or hospitality sales management may be considered in lieu of a degree. 
• Minimum 5–7 years of progressive sales leadership experience in the hospitality, resort, or events industry.

PHYSICAL DEMANDS AND WORKING ENVIRONMENT:

• This is an office position but may require carrying up to 40 lbs and/or walking in winter conditions
• Must be able to work occasional evenings, weekends, and travel as required for events, trade shows, and client meetings.

BENEFITS OF WORKING AT WINTERGREEN:

Wintergreen Resort is a place for mountain lovers, adventure seekers and outdoor explorers.  A place to chase new experiences, marvel at the unexpected, and build new relationships that will keep you coming back for more. We work to play!  We work in a fun-filled, beautiful resort setting and have a competitive compensation with a comprehensive benefit portfolio for full-time year-round associates: (Medical, Dental, Vision, Life, Short and Long Term Disability Insurances as well as Paid Time Off and a 401K plan).  Our unique Recreational Benefit Package offers associates free and/or discounted resort activities, services and products.  

We have many fantastic opportunities available from our spectacular, sweeping mountain slopes to our beautiful valley and lake.  If this position isn’t quite what you are looking for, please visit our career page for even more open positions: Wintergreen Resort: Premier Blue Ridge Mountain Ski, Golf, Tennis, Spa and Family Vacation Resort in Virginia.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability status or any other characteristic protected by applicable law.

Essential functions, as defined under the Americans with Disabilities Act, may include any of the following representative duties, knowledge, and skills. This is not a comprehensive listing of all functions and duties performed by incumbents of this position; employees may be assigned other duties which are not listed below; reasonable accommodations will be made as required.   The job description does not constitute an employment agreement and is subject to change at any time by the employer. Essential duties and responsibilities may include, but are not limited to the following: