Maintenance Technician

Two Pines Properties

Keep Big Sky Running Smoothly - All Year Long

Epic mountain views, fresh air, the ultimate adventure backdrop

Year-round
Posted: Jun 25, 2025

Maintenance Technician

Location
Big Sky, Montana
Wages/Pay
$21.00 - $26.00 / hour
Experience Level
Some experience required
Job Start Date
Job Starts: Jun 26, 2025

Ready for a year-round job where your work actually matters — and the mountains are your backyard? We’re looking for a Maintenance Technician to join our tight-knit crew in Big Sky. You’ll be part of a supportive, hands-on team that’s all about delivering great guest experiences — and having fun while doing it. Plus, we hook you up with employee housing that feels like home. If you're hands-on and thorough, dependable, and down for a role full of variety, fresh air, and mountain-town vibes — this is your chance to live and work in the best place on Earth: Big Sky, Montana.

Job Summary:
As a Maintenance Technician, you’ll be the behind-the-scenes problem solver keeping our homes running smoothly. From fixing a leaky faucet to troubleshooting appliances, patching drywall, or adjusting a door — your work ensures every home is safe, functional, and guest-ready. You’ll use maintenance software on your phone to track and complete tasks efficiently, and you’ll communicate professionally with guests, owners, and vendors when needed. Most of your time will be spent inside the homes themselves, working independently across our Big Sky portfolio. Tasks may also include painting, power washing, roof raking, and small upgrades — all essential parts of the role that help us maintain high-quality homes year-round.

What You'll Be Up To: 

As the go-to problem solver, your main tasks will include:

  • Responding to maintenance requests and completing work orders across our portfolio of high-end vacation homes

  • Troubleshooting and repairing basic plumbing, electrical, and appliance issues

  • Handling light carpentry work — like adjusting doors, fixing trim, or tightening up cabinetry

  • Performing drywall patches, touch-up painting, and other cosmetic fixes as needed

  • Using maintenance software on your phone to track tasks and stay organized

  • Keeping an eye out for safety or property concerns and reporting them proactively

  • Communicating with guests, homeowners, and vendors in a friendly, professional way

  • Pitching in on seasonal projects like snow removal, power washing, or painting

  • Helping with the occasional trash run between guest stays to keep things fresh and guest-ready

  • Taking care of everyday fixes — like swapping light bulbs and tackling those small but important household details that keep everything running smoothly

  • Taking pride in every finished task — big or small — and helping keep Big Sky homes guest-ready year-round

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

  • Basic home maintenance knowledge and the ability to problem-solve on the fly

  • Mechanically inclined and confident using tools — you’ll need your own basic toolkit (think: screwdrivers, drill, wrenches, tape measure, etc.)

  • 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 provide a reimbursement every pay period for phone use

  • Solid time management skills — staying organized and efficient across multiple properties

  • Physical ability to lift 50+ lbs, bend, crouch, kneel, and stand for extended periods while working indoors and occasionally outdoors

  • A valid driver’s license and a clean driving record (at least 3 years) — you’ll be cruising Big Sky in a company vehicle

  • Flexibility to work a schedule that includes weekends and holidays — but only day shifts

  • A can-do attitude — when we say we’ve got each other’s backs, we really mean it

  • Available to be on-call with the team — super rare issues like no heat, flooding, or propane outages may come up, but there’s no need to stay glued to your phone or change your plans. Calls are rotated fairly across the entire team

  • Willing to sign an NDA and non-compete — just our way of keeping things professional and protecting the work we do

  • Ability to pass a background check

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 the start of your new beginnings in Big Sky!

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 a little flexibility when the mountains call

  • Use of a company vehicle during your shift

  • Cell phone reimbursement, included in every pay period

  • 120 hours of PTO ready to use — just request ahead and stay on top of your schedule

  • Daily variety — no two shifts are the same

  • Affordable employee housing right in Big Sky — no long drives from Bozeman

  • Work across different properties each day — mostly indoors, sometimes outdoors, always moving

Plus, year-round benefits:

  • Employee health benefits available after 50 days — including medical, dental, and vision through Horizon BCBS (we cover 75% of the bronze-level health plan)

  • 401(k) with company match available after 6 months

  • Annual raises are automatically given on your work anniversary based on the governments COLA (cost of living adjustment) rate, and you may also earn merit-based raises along the way - those aren't on a set schedule, just recognition when it's earned

  • Winter Perk Options after 6 months:

    • Choose a Big Sky Resort Winter Season Pass (with some fine print — ask us for details)

    • Or opt for a Health & Wellness reimbursement added to each paycheck

Lets Grow Together:

We're offering $21-$26/hour, depending on experience. Got basic home maintenance knowledge, a solid work ethic, and a willingness to learn? We offer light training and support - and we're excited to find someone who's ready to grow with us over time. 

If this sounds like your next chapter, we'd love to hear from you. Apply now and get ready to be apart of something special in Big Sky. 

How to Apply

Interested? Just email your resume to kellyanne@twopines.com

We're excited to get to know you and hopefully welcome you to the crew!  

Contact Info

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