Two Pines Properties
July 8, 2022
anywhere, United States of America
Job Type
$17.00 plus seasonal bonuses based on company performance



Two Pines Properties is the largest locally owned and operated vacation rental company in Big Sky, Montana. Wes & Alex Hoecker, husband, and wife-duo, started the company in 2014 with a single 2-bedroom condo and have quickly grown to be one of the most successful property management companies in the Big Sky area with over 95, extreme-luxury residences. A number that increases almost weekly. Two Pines Properties has been voted 'Best Property Management Company' by Explore Big Sky Magazine for 3 years, consecutively. In a resort community steeped with competition in the vacation rental market, Two Pines Properties stands out with a simple yet powerful leading motivation: to provide the best possible service. Two Pines Properties cares deeply about the partnerships they have with their clients and community and attacks goals, issues, and growth with a relational mindset. The Two Pines Team is hungry, innovative, and quite frankly, a force to be reckoned with. Our work culture is healthy and dynamic with an intentional focus on positivity and communication. Life is short, love where you work!


The Vacation Rental Operations Specialist role is the 'first impression' of Two Pines! Demeanor, attitude, and communication skills are all vitally important. This role is responsible for coordinating with other team members to ensure that vacation rental guests and Two Pines clients are provided with an exceptional level of service. This individual will work with multiple areas of the company (vendors, bookkeepers, accountants, guests, clients, and other staff). Incoming reservations and reservation requests are also handled by this person. Therefore, excitement about the Big Sky area and our properties is a necessity in order to secure that booking! This is a dynamic position with responsibilities varying at different times of the month and seasons!


  • Build comprehensive vacation rental listings by compiling information from various sources on multiple platforms. Once listings are built, keep them up to date and accurate.
  • Respond to and direct all incoming office phone calls.
  • Process and track tenant rent payments for long-term rental properties.
  • Respond to incoming reservation requests on various OTAs (Online Travel Agencies) platforms, phone inquiries, and emails in a timely, positive, and comprehensive manner.
  • Communicate information to confirmed and potential guests about the property, the surrounding area, and local attractions/events via email or telephone.
  • Develop and maintain positive guest communication prior to arrival, verifying the guest has the appropriate information to make for a smooth arrival and stay.
  • Communicate with appropriate individuals or departments (e.g., Contractors, Housekeeping, Maintenance) as necessary to resolve guest/tenant/client issues.
  • Client services- Communication with clients regarding their property, financial statements, and navigation through their client portal online.
  • Select bookkeeping items- Organize invoices for payment and gather information needed for tax remittance.



  • Hospitality industry experience required.
  • Experience with OTA's such as VRBO and Airbnb is a plus.
  • Experience in guest services, reservations, or operations in the vacation rental industry is preferred.
  • Knowledge of the Big Sky, Montana area is strongly desired.
  • Strong knowledge of Gmail, Google Docs, Google Sheets, and Excel.
  • Must be able to quickly adapt to effectively using multiple guest reservation platforms and software.
  • Must be dependable and have the flexibility to work on weekends, nights, and/or holidays based on business demands.


Hourly: $17.00 plus seasonal bonuses based on company performance.

Bonus Details: Seasonal bonuses based on company performance.


  • Remote anywhere in the U.S.
  • Paid time off such as PTO, sick days, and vacation days
  • Health Insurance
  • Retirement benefits or accounts
  • Growing with an amazing team in a beautiful location!

Two Pines Press Releases:

Best of Big Sky- Explore Big Sky

The Views Magazine

Vimeo about Two Pines