Glamping Transportation Supervisor - Seasonal Summer 2027

We Inspire People to Be More Alive 

About Paws Up Montana:

Paws Up Montana, America’s premier luxury ranch resort, is more than a workplace—it’s a chance to be part of something extraordinary. 

Our most successful employees are those who are self-motivated, confident leaders with strong organizational skills. They thrive in dynamic environments, motivate teams, and lead by example in the field. A love of the outdoors and an adventurous spirit are crucial. The desire to create structure, build trust, and go above and beyond is what makes our Resort so special.

Position: Seasonal April-October

Join the Team Behind the Most Iconic Wilderness Experience in Montana 

 At Paws Up Montana, the Glamping Transportation Supervisor role is more than a job—it’s about leading from the front. This role is for hands-on leaders who thrive on teamwork, logistics, and guest-focused problem solving in a one-of-a-kind wilderness setting. 

You’ll oversee on-property transportation within the Glamping department, supervising a large fleet of vehicles and a seasonal team of Drivers. You’ll be out in the field every day, ensuring the seamless flow of guests, staff, and supplies across six luxury camps and signature outdoor dining events. 

What We Offer: 

• Career Development and Advancement Opportunities
• Employee Assistance Program(5 free counseling sessions)
• Referral Bonus Program(Get paid $250 to recruit)
• Carpool Reimbursement($5-$20/Day)
• Employee Discounts on Merchandise(30% on select items in our retail store)
• Employee lunch provided

Primary Responsibilities: 

Lead the Transportation Team

• 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.

Oversee Operations

• 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.

Ensure Service Excellence

• 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.

Work Shoulder-to-Shoulder

• Assist with shuttles, runs, and deliveries as needed.

• Lead by example: no task is too small, and no team member works alone.

Who You Are:

• Organized and detail-oriented while flexible enough to adapt to shifting needs.

• Calm under pressure, proactive in solving problems, and quick to make decisions.

• Experienced in transportation, logistics, or hospitality with prior leadership 

responsibility.

• A natural communicator who values teamwork and accountability.

• Comfortable working outdoors in a remote Montana setting.

Bonus Points If You:

• Have a CDL or advanced driving credentials.

• Have managed seasonal or large teams before.

• Enjoy mentoring and developing staff in real time.

• Thrive in high-volume environments where structure and adaptability are equally 

important.

A Quick Reality Check 

This role is not for you if you prefer to manage from behind a desk, avoid getting your hands dirty, or hesitate to give feedback in the moment. But if you thrive on being in the field, love leading teams, and want to create structure in a fast-paced, guest-focused environment—we’d love to meet you

Paws Up Montana provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.