Glamping Transportation Supervisor - Seasonal Summer 2027

Position Summary

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 Key Responsibilities Field Leadership & Staff Mentorship: 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. Transportation & Fleet Operations: 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. Quality Assurance & Standards: Perform active field audits of guest service standards; address service gaps or operational delays immediately with constructive, real-time coaching. Hands-On Operational Support: Lead by example by directly assisting with guest shuttle runs, vehicle detailing, luggage transfer, and field logistics during peak activity times. Guest Relations & Problem Solving: 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. Safety & Compliance: Enforce property safety protocols, speed limits, off-road driving guidelines, and Montana motor vehicle regulations across all transportation activities. Ad-Hoc Duties: Perform additional operational tasks and field projects as assigned by Glamping Leadership.

Qualifications

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). Specialized Knowledge: Deep understanding of fleet routing, driver management, vehicle safety, and luxury guest service standards in a remote or resort environment.

Core Skills: Strong leadership, active communication, conflict resolution, and organizational skills; calm under pressure with a proactive approach to dynamic field operations. Technical & Licensing Requirements: 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.

Work Style: Highly energetic, adventurous, and comfortable working outdoors in varying Montana weather conditions; willing to handle hands-on physical work alongside staff. Physical Requirements Mobility & Outdoor Exposure: 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.

Scheduling: Ability to work a seasonal schedule (May through October), including early mornings, late evenings, weekends, and holidays as required by resort guest volume. Lifting & Vehicle Operations: 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.

This job description is intended to convey information essential to understanding the scope of the position and is not intended to be an exhaustive list of skills, efforts, duties, responsibilities, or working conditions associated with the position. Management may assign or reassign duties and responsibilities to this job at any time.

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.