JOB DESCRIPTION

POSITION:                 Director of Lodging and Rental Operations

FLSA:                         Exempt

REPORTS TO:           General Manager

SUMMARY: The Director of Lodging & Rental Operations is responsible for leading all aspects of lodging operations, including the Front Desk, Housekeeping, Rental Properties, Public Areas, and Facilities (Janitorial), while also driving growth of the resort’s rental property inventory. This position balances operational leadership to deliver positive guest experiences with a proactive role in owner relations and sales, ensuring properties are well-maintained, service standards are met, and the rental program continues to expand. The role is essential to maintaining Wintergreen’s reputation as a premier, four-season mountain resort by ensuring rental inventory meets both guest expectations and revenue goals.

The Director motivates and develops staff, maintains strong relationships with rental owners, and ensures guest service feedback and surveys are actively used to improve operations. Success requires a results-driven leader who can deliver fully enjoyable and memorable guest experiences while maintaining cost controls, and who can actively market and sell the resort’s rental program to property owners.

PRIMARY RESPONSIBILITIES

Operational Management

• Direct daily operations of the Front Desk, Housekeeping, Rental Properties, Public Areas, and Facilities (Janitorial) to ensure consistent service, safety, and cleanliness.
• Enforce resort policies and procedures, including safety, security, and key control standards.
• Oversee property management systems, ensuring accuracy in reservations, owner accounts, and reporting.
• Leverage guest feedback and satisfaction data to proactively identify service improvements and operational training needs.
• Ensure smooth integration of guest services and rental operations, maintaining alignment with resort standards.

Rental Property Growth & Owner Relations

• Actively promote the resort’s rental program to property owners, highlighting benefits and building trust to grow participation.
• Serve as the primary contact for rental property owners, addressing concerns and ensuring satisfaction with the program.
• Manage onboarding of new properties, coordinating inspections, contracts, and integration into the rental pool.
• Develop and implement strategies to expand and enhance the rental property portfolio, aligning inventory with evolving guest trends and revenue targets. 

Leadership & Staff Development

• Recruit, hire, train, and mentor staff across lodging departments, ensuring they are equipped to deliver exceptional service.
• Motivate team members through clear communication, recognition, and professional development opportunities.
• Set measurable performance goals for staff and conduct regular evaluations with feedback and coaching.
• Foster a positive, accountable, and collaborative workplace culture.
• Encourage cross-training across departments to support a flexible, well-rounded lodging team.

Financial & Business Management

• Manage departmental budgets, labor costs, and financial performance, balancing efficiency with service standards.
• Review key performance reports, including occupancy, ADR, and rental revenue, to ensure targets are achieved.
• Implement cost-control measures while maintaining guest and owner satisfaction.
• Provide senior leadership with data-informed insights, accurate reporting and recommendations for operational and revenue improvements.

Cross-Department Collaboration

• Partner with Marketing to promote the resort’s rental program and highlight the benefits of owner participation.
• Work with Maintenance, Housekeeping, and Operations teams to ensure properties are consistently guest-ready.
• Collaborate with Sales, F&B, and Recreation teams to ensure lodging supports broader resort activities and events.
• Actively participate in leadership meetings, aligning lodging and rental operations with resort-wide goals.
• Engage with Marketing and the resort General Manager on the revenue management team to drive lodging revenue.

MINIMUM QUALIFICATIONS:

• Leadership & Team Management: Proven ability to lead and motivate teams, while handling personnel issues and conflict resolution diplomatically.
• Hospitality Operations Experience: Familiarity with Springer-Miller, Medallia, or comparable hospitality property management and guest experience systems preferred. 
• Financial Oversight: Skilled in budgeting and managing multi-unit lodging operations, with a strong understanding of cost control, payroll, and revenue performance.
• Communication & Crisis Management: Excellent verbal and written communication skills with the ability to manage high-pressure or emergency situations calmly and effectively.
• Guest & Owner Relations: Strong public relations skills with a guest-first mindset; capable of managing owner relationships and resolving concerns with professionalism.
• Service Standards & Operational Excellence: Committed to upholding hospitality standards, maintaining clean and safe public areas, and ensuring staff deliver a high level of service consistently, even during peak periods or under pressure. 
• Flexibility & Availability: Must be able to work a flexible schedule, including weekends and holidays, and be accessible to staff as needed during off-hours.

EDUCATION, TRAINING AND EXPERIENCE GUIDELINES:

Degree or coursework in Business, Hospitality, or a related field preferred; equivalent combination of education and relevant work experience will be considered.

LICENSE AND CERTIFICATION REQUIREMENT(S):

PHYSICAL DEMANDS AND WORKING ENVIRONMENT:

• Must be able to stand on feet for an eight hour shift. 
• Must exercise caution with computer equipment.  
• Must be able to lift up to 25 pounds.  

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.