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Ready for a seasonal job where your work actually matters—and the ski slopes are your backyard? We’re looking for a Seasonal Operations Specialist - Property Inspector to join our tight-knit crew for the Summer 2026 season in Big Sky. You’ll be part of a chill, supportive team that’s all about making guests happy and having fun doing it. If you’re dependable, detail-focused, and ready for a summer full of variety, long sunny days, and mountain adventures, this is your chance to live, work, and explore the best place on Earth: Big Sky, Montana.
Job Summary:
You’ll be the go-to person making sure every vacation home is guest-ready, from inspections before check-in to keeping supplies and vehicles stocked. You’ll report maintenance or cleaning issues, help with guest deliveries, and jump in with light maintenance like painting, power washing, housekeeping, or refreshing property signage when things slow down. You’ll work mostly solo, driving a company vehicle around Big Sky, spending your days on the move, and enjoying the views. No two days are the same, and teamwork makes it all run smoothly. The job starts mid April, and runs through late October. (dates are flexible)
What You'll Be Up To:
As the go-to person for property readiness, your main tasks include:
Conducting thorough inspections before guest check-in and after check-out to ensure homes are well-stocked, properly cleaned, and everything is in working order.
Managing inventory for both properties and designated company vehicle(s) - keeping supplies stocked and reporting what's needed.
Identifying and promptly reporting maintenance or cleaning issues to the right teams for fixes.
Assisting with light maintenance tasks, such as replacing bulbs, adding rug tape, removing trash, adding pads to chairs, etc.
Handling in-house guest deliveries - making sure guests get what they need on time with a friendly attitude.
Working mostly independently, driving a company vehicle around Big Sky to different properties.
Communicating clearly and working collaboratively with team members to keep operations running smooth and effectively.
Using a mobile app on your phone to complete tasks and keep updates flowing throughout the day.
What You'll Need:
A strong work ethic and the confidence to roll up your sleeves and get things done - mostly on your own.
Clear and friendly communication skills - you'll be chatting with teammates, guests and owners to keep things running smoothly.
An eagle eye for spotting maintenance, cleaning or stocking needs.
Comfortable using your personal smartphone to download a free app from the App Store and use it throughout the day to tackle tasks and stay updated - we even provide a reimbursement every pay period for phone use.
The stamina to be on your feet, moving around properties, and pitching in with light maintenance when needed.
A valid driver's license and a clean driving record (of at least 3 years) - because you'll be behind the wheel of a company vehicle, cruising Big Sky.
Flexibility to work a seasonal schedule that includes weekends and holidays - with only day shifts.
A can-do attitude - when we say we've got each other's backs, we really mean it.
Ability to pass a background check.
Confidence driving in winter conditions - snow, ice, and mountain roads are part of everyday, so solid driving experience is a must.
Where You'll Crash:
Forget cramped bunks or condos packed with a dozen people - our affordable employee housing actually feels like home. All of our spots are right in the heart of Big Sky - not Bozeman, or Four Corners - so you're close to everything making this place special. You'll get your own private bedroom in either a townhome or a full-size house, with plenty of room to kick back after a day of adventure. Each property has a full size kitchen, multiple bathrooms and at minimum two full-size fridge/freezers. Want a mini fridge in your room or a locked door with your own key? No problem - we'll hook you up. We keep things fair with monthly inspections to make sure everyone's doing their part to keep common areas clean and comfy. Plus, all roommates pass a background check - just making sure we know who's sharing the space.
Because this isn't just a job - it's your summer home away from home.
Perks of the Mountain Life:
It comes with more than just a paycheck (though that's pretty great too). Here's what's in it for you:
40 hours/week on average (plus some flexibility when the mountains call)
Use of company vehicle during your shift
Cell phone reimbursement, included in every pay period
Daily variety - no two shifts are the same
Affordable employee housing - right in Big Sky! no long drives from Bozeman
Spend your days moving around Big Sky - working both indoors and outdoors - and being in different properties everyday
Plus, the chance to stay on with us as part of the next seasonal crew and keep the adventure going all year!
How to Apply
Please email your resume to Bradley@twopines.com
Contact Info
- Kellyanne Harrington
- kellyanne@twopines.com
- (406) 995-2299
- www.TwoPines.com
Two Pines Properties
We’re all about keeping it local, real, and rooted in Big Sky. As the largest locally owned vacation rental company, we take pride in smooth guest stays and a team that feels like friends. Trust, teamwork, and good vibes guide us. If you want your work to matter and love the mountain life, you’re home.
