Glamping Transportation Supervisor – Seasonal

• Schedule, coach, and support Drivers to ensure smooth coverage
• Provide real-time feedback and role-model professional service in the field
• Recruit, train, and mentor seasonal staff to build strong communication and trust
• Supervise daily transportation for staff, supplies, alcohol weigh-outs/returns, and event dinners
• Maintain and audit a large seasonal fleet in collaboration with the resort’s Transportation team
• Balance staff and guest needs by making quick, thoughtful decisions under pressure
• Audit service standards in the field and address issues immediately
• Reinforce positive behaviors and create structure staff can rely on
• Foster a culture where staff feel supported, safe, and empowered
• Assist with shuttles, runs, and deliveries as needed
• Lead by example in a hands-on field role

• Self-motivated, confident leader with strong organizational skills
• Love of the outdoors and an adventurous spirit
• Experience in transportation, logistics, or hospitality with prior leadership responsibility
• Organized and detail-oriented, while flexible enough to adapt to shifting needs
• Calm under pressure, proactive in solving problems, and quick to make decisions
• Natural communicator who values teamwork and accountability
• Comfortable working outdoors in a remote Montana setting
• CDL or advanced driving credentials preferred as a bonus
• Experience managing seasonal or large teams preferred as a bonus
• Enjoy mentoring and developing staff in real time
• Ability to thrive in high-volume environments where structure and adaptability are equally important

Demonstrates strong leadership and organizational skills in managing transportation logistics and seasonal staff, fostering a supportive and adaptable work environment. Proficient in real-time problem-solving and decision-making while maintaining high service standards in outdoor settings.

• Transportation Management
• Team Leadership
• Real-Time Problem Solving
• Staff Training and Mentoring
• CDL or Advanced Driving Credentials

• Transportation Logistics
• Fleet Maintenance
• Service Standards Auditing
• Event Coordination
• Decision Making Under Pressure

• Strong Communication
• Organizational Skills
• Adaptability
• Teamwork
• Empathy

• CDL or Advanced Driving Credentials

• Hospitality
• Seasonal Staff Management
• Outdoor Work Environment
• High-Volume Operations
• Staff Empowerment