Two Pines Properties
November 1, 2022
Big Sky, Montana
Job Type
Annual Salary: $100,000.00 - $125,000.00 with on track earning of $200K-$250K OTE



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 85 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: 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, frankly, a force to be reckoned with. Our work culture is healthy and dynamic, with an intentional focus on positivity and communication.


Affordable Housing and Relocation Assistance to Big Sky, MT is available for the right applicant.

The General Manager at Two Pines Properties will report directly to the owners and collaborate with all members of the company: operations, maintenance, guest services, and administration. The GM will also spearhead client satisfaction and new client onboarding care. With the level of immense growth Two Pines is experiencing, the General Manager will be crucial in helping maintain quality control for clients and guests alike.

In the vacation rental world, every day can look different. Property maintenance issues can create an entirely different workflow for the day than an internal systems review day. The day can be entirely on the computer or around the Big Sky area, meeting with clients, vendors, or guests. It's dynamic.


Responsibilities are to:

  • Demonstrate a full commitment to providing the best possible experience for clients, guests, and employees.
  • Responsible for maximizing revenues with efforts to retain staff and achieve high return-guest outcomes.
  • Monitor inventory of supplies both for office and properties.
  • Research and implement systems to help the company with efficiency and revenue goals.
  • Ensure that all guest and client-related issues are resolved in a manner consistent with the company goals and objectives.
  • Recruit, train, and coach qualified applicants.
  • Communicate all policies and procedures to staff.
  • Conduct regular meetings with staff to provide various information, including companywide goals and expectations.
  • Build solid client relationships in the Big Sky area as well as with other managers and staff.
  • Adhere to federal, state, local, and employment-related laws and regulations.


  • Proven experience as a General Manager or similar Executive role in the hospitality industry.
  • Previous experience in the vacation rental industry is strongly preferred.
  • Knowledge of vacation rental business processes and functions such as guest services, owner relations, and revenue management.
  • Strong analytical ability with excellent communication skills.
  • BSc/BA in Business or relevant field


Annual Salary: $100,000.00 - $125,000.00 with  $200K-$250K OTE

Bonus Details: Annual bonuses are available with a review of KPIs and annual evaluations, including merit and COLA considerations and market adjustments for cost of living.


  • Affordable housing is available in Big Sky, MT.
  • Paid time off includes PTO, sick, and vacation days.
  • Health insurance.
  • Retirement benefits or accounts.
  • Commuting/travel assistance.
  • Workplace perks such as recreation activities, food and coffee, and flexible work schedules.
  • Use of company vehicle when available.
  • Season Ski Pass.

Two Pines Properties Press Releases