Glamping Transportation Supervisor - Seasonal Summer 2027

Paws Up Montana • Greenough, MT

68d • Onsite

About The Position

The Glamping Transportation Supervisor is a seasonal, hands-on field leader responsible for overseeing daily guest and team transportation logistics across Paws Up Montana’s luxury glamping camps, activity centers, and signature outdoor dining venues. Managing a large seasonal fleet and supervising a dedicated team of Drivers, this role operates directly in the field to ensure smooth operational flow, strict safety standards, and flawless guest transportation service. The ideal candidate thrives outdoors in a high-volume wilderness environment, leads shoulder-to-shoulder with their team, and balances operational structure with fast-paced problem solving. This is a seasonal role April - October 2027.

Requirements

• Minimum 2–3 years of experience in transportation, fleet logistics, guest services, or outdoor recreation, including at least 1 year in a supervisory or team lead capacity (experience leading seasonal teams preferred).
• Deep understanding of fleet routing, driver management, vehicle safety, and luxury guest service standards in a remote or resort environment.
• Strong leadership, active communication, conflict resolution, and organizational skills; calm under pressure with a proactive approach to dynamic field operations.
• Valid State Driver’s License with a clean driving record (CDL or advanced passenger driving credentials preferred); basic proficiency with digital scheduling tools and communication devices.
• Highly energetic, adventurous, and comfortable working outdoors in varying Montana weather conditions; willing to handle hands-on physical work alongside staff.
• Ability to work outdoors in variable wilderness weather conditions (heat, rain, dust, cold) and remain on your feet, moving actively across outdoor terrain and resort facilities for extended shift periods.
• Ability to work a seasonal schedule (May through October), including early mornings, late evenings, weekends, and holidays as required by resort guest volume.
• Ability to frequently sit, drive, climb in and out of multi-passenger vehicles, and lift or carry guest luggage and detailing equipment weighing up to 50 lbs.

Nice To Haves

• experience leading seasonal teams preferred
• CDL or advanced passenger driving credentials preferred

Responsibilities

• Supervise, support, and mentor seasonal Drivers; monitor daily shift schedules, staffing levels, and real-time field performance to build a culture of accountability, trust, and service excellence.
• Direct daily shuttle and dispatch operations across all six luxury camps, activity hubs, and dining events; conduct routine audits and inspections of the seasonal vehicle fleet to ensure cleanliness, fuel levels, and safety compliance.
• Perform active field audits of guest service standards; address service gaps or operational delays immediately with constructive, real-time coaching.
• Lead by example by directly assisting with guest shuttle runs, vehicle detailing, luggage transfer, and field logistics during peak activity times.
• Serve as a primary point of contact for transportation-related guest inquiries or schedule shifts, making quick, thoughtful decisions under pressure to maintain an effortless guest experience.
• Enforce property safety protocols, speed limits, off-road driving guidelines, and Montana motor vehicle regulations across all transportation activities.
• Perform additional operational tasks and field projects as assigned by Glamping Leadership.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed