Glamping Transportation Supervisor

Knightsbridge Capital Corporation • Greenough, MT

8h • Onsite

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

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

Benefits

• 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

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed