Property Inspector - Live and work where others only get to vacation.

The Property Inspector ensures Two Pines vacation rental properties are clean, stocked, safe, functional, and guest-ready before arrivals and after departures. This role includes completing detailed property inspections, reporting maintenance and housekeeping concerns, restocking supplies, assisting with guest deliveries, and supporting light property care tasks as needed. 

This is an in-person, field-based position in Big Sky, Montana. The Property Inspector will work independently throughout the day, travel between properties using a company vehicle during scheduled shifts, and use company software/mobile applications to document work,  communicate updates, and complete assigned tasks. 

• Complete detailed pre-arrival and post-departure inspections to confirm properties are clean, stocked, guest-ready, and in good working order. 

• Identify and report maintenance, housekeeping, stocking, safety, or guest-readiness concerns to the appropriate team members. 

• Restock property supplies and maintain inventory for assigned properties and designated company vehicles. 

• Assist with guest deliveries and in-house requests in a timely and professional manner. 

• Complete light hands-on property care tasks as needed, including replacing light bulbs,  removing trash, adding rug tape, adding furniture pads, refreshing property signage, light painting, power washing, light housekeeping support, and other basic property support tasks. 

• Communicate clearly with team members regarding property status, inspection results,  guest needs, and follow-up items.

• Use a mobile app and company systems to complete tasks, upload photos, document notes, and provide real-time updates throughout the workday. 

• Operate a company vehicle during scheduled shifts and travel between properties throughout Big Sky. 

• Work both independently and collaboratively to support daily operations and maintain  Two Pines property standards. 

• Assist with other seasonal operations needs as assigned. 

Skills: 

• Strong attention to detail and ability to identify cleaning, stocking, maintenance, and guest-readiness concerns. 

• Dependable, self-motivated, and comfortable working independently throughout the day. 

• Clear, professional communication skills with team members, guests, vendors, and homeowners as needed. 

• Ability to use a personal smartphone and company-provided software/mobile applications throughout the workday. 

• Ability to remain active during the workday, including standing, walking, climbing stairs,  lifting, carrying, and moving between properties. 

• Ability to lift and carry up to 50 lbs as needed. 

• Comfortable completing minor hands-on property care and light maintenance support tasks. 

• Valid driver’s license and clean driving record for at least the last three years. 

• Comfortable driving in Big Sky, including mountain roads and changing weather conditions.

• Flexible and team-oriented attitude, with availability to work weekends and holidays as scheduled. 

• Ability to successfully complete a background check and Motor Vehicle Record check.