Glamping Transportation Supervisor - Seasonal Summer 2027

Knightsbridge Capital Corporation; Greenough (MT); On-site; USD 2,755,000 - 4,133,000; Full time

Benefits offered by this job

Career development

Employee assistance program

Referral bonus ($250)

Carpool reimbursement

Employee discounts

Lunch provided

Job summary

Paws Up Montana is seeking a Glamping Transportation Supervisor for the Seasonal Summer 2027 period. This hands-on leadership role oversees a large fleet and a seasonal driver team, ensuring smooth guest, staff, and supply movements across six luxury camps.

Ideal candidates are organized, calm under pressure, and experienced in transportation, logistics, or hospitality with prior leadership responsibilities. Outdoor work in remote Montana is expected.

Qualifications

• Leadership experience in transportation, logistics or hospitality.
• Ability to supervise seasonal teams and manage field operations.
• Excellent communication and problem-solving under pressure.
• Comfortable working outdoors in remote Montana settings.

Responsibilities

• Lead the Transportation Team with schedule coaching and coverage.
• Oversee daily transport for staff and guests and balance needs under pressure.
• Maintain and audit a large seasonal fleet in coordination with the resort team.
• Recruit, train and mentor seasonal drivers and staff.
• Assist with shuttles, runs and deliveries as needed.

Skills

Leadership experience

Transportation logistics

Hospitality knowledge

Team coaching

Communication skills

Job description

If you are unable to complete this application due to a disability, contact this employer to ask for an accommodation or an alternative application process.

Glamping Transportation Supervisor - Seasonal Summer 2027

Seasonal Management Ruff MT, Greenough, MT, US

2 days ago Requisition ID: 5181

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’sa 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
• 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.

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 UpMontanaprovides 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.