Business Operations & Human Resources Manager
Two Pines Properties | Big Sky, Montana
Full-Time | On-Site- Some Remote Flexibility
$80,000–$95,000 annually, DOE
About the Role
Two Pines Properties is seeking an experienced, highly organized Business Operations & Human Resources Manager to support the day-to-day infrastructure of our growing vacation rental management company in Big Sky.
This is a hands-on management position for someone who thrives in a dynamic small-business environment and enjoys solving problems, improving systems, supporting employees, and keeping the many moving pieces of an organization running smoothly.
The position works closely with company ownership and department leaders and serves as a central resource across human resources, payroll, employee housing, technology, administrative operations, client onboarding and offboarding, and company-wide processes.
This is not a narrowly defined corporate HR position. We are looking for a versatile operator who can move comfortably between people, systems, paperwork, technology, properties, and operational priorities.
Key Responsibilities
Human Resources & Payroll
- Coordinate employee onboarding and offboarding, including employment documentation, background checks, system access, company equipment, and employee records.
- Prepare and administer bi-weekly payroll.
- Coordinate employee benefits, including health insurance, retirement benefits, and other company programs.
- Maintain personnel records and employee documentation.
- Assist ownership and department leaders with recruiting, job postings, offers, training documentation, and employee policies.
- Maintain and update the Employee Handbook, company policies, agreements, and internal documentation.
- Coordinate with the company's outside HR, insurance, accounting, and legal professionals as directed by ownership.
- Help ensure company employment practices and procedures remain compliant and well documented.
Business & Administrative Operations
- Identify operational gaps and help ownership develop practical systems, SOPs, policies, and workflows.
- Maintain organized company records and documentation.
- Coordinate vendor documentation, W-9s, payments, deposits, and other administrative accounting functions.
- Assist with licensing, permits, inspections, and compliance requirements for managed properties.
- Support ownership with special projects, research, documentation, and company initiatives.
- Help create training materials, department manuals, instructions, and internal resources.
Client & Property Administration
- Manage the administrative onboarding process for new vacation rental properties from signed management agreement through launch.
- Coordinate documentation, photography, property information, access information, signage, internal systems, and required onboarding materials.
- Coordinate the administrative offboarding process for properties leaving management.
- Maintain accurate records and ensure information is communicated across departments throughout property transitions.
Employee & Long-Term Housing
- Assist with administration of company employee housing and other long-term rental units.
- Coordinate leases, rent collection, deposits, move-in/move-out documentation, inspections, maintenance requests, and housing records.
- Work with Operations and ownership to address housing issues as they arise.
Technology & Systems
- Administer employee access to company technology platforms and systems.
- Coordinate setup, distribution, recovery, and reassignment of company computers and other technology.
- Provide basic internal technology troubleshooting and coordinate outside assistance when needed.
- Help ensure company systems, accounts, and sensitive information remain organized and secure.
- Maintain familiarity with the company's operational technology, including property-management, communications, scheduling, and productivity platforms.
Company-Wide Support
- Serve as a trusted resource for department leaders and employees.
- Assist departments during periods of high demand or staffing shortages.
- Help coordinate company meetings, events, training, and internal initiatives.
- Maintain a professional and organized office environment.
- Build strong relationships with employees, homeowners, vendors, and community partners.
- Proactively identify problems and bring proposed solutions to ownership.
Who We're Looking For
The successful candidate will be exceptionally organized, resourceful, trustworthy, and comfortable taking ownership of projects from beginning to end.
Preferred qualifications include:
- 3+ years of experience in business operations, human resources, hospitality management, property management, office management, or a related field.
- Experience with payroll, benefits administration, employee onboarding, or HR processes.
- Strong technology skills and the ability to learn new software quickly.
- Excellent written and verbal communication.
- Strong judgment and discretion when handling confidential employee and company information.
- Demonstrated ability to prioritize multiple projects and deadlines without losing attention to detail.
- Ability to create and improve processes rather than simply follow existing ones.
- Hospitality, vacation rental, property management, or small-business experience is strongly preferred.
- Familiarity with platforms such as Track PMS, Paylocity, Monday.com, Breezeway, Google Workspace, WordPress, or similar systems is a plus.
- Must be comfortable working on-site in Big Sky and occasionally visiting company-managed properties.
The Right Fit
Two Pines is a locally owned company, and this position is particularly important to our organization. We are looking for someone who wants to understand how the entire business operates, not simply one department.
The right person will see something that isn't working, investigate why, communicate effectively with the people involved, and help build a better process. They will be equally comfortable helping an employee navigate onboarding, coordinating a new property launch, troubleshooting a company system, reviewing documentation, or organizing a company-wide initiative.
This role is ideal for someone who enjoys variety, responsibility, autonomy, and being the person who helps keep an organization moving forward.
Compensation: $80,000–$99,000 annually, depending on experience.
Two Pines Properties is an Equal Opportunity Employer.
Pay: $80,000.00 - $95,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Employee discount
- Health insurance
- Paid time off
- Relocation assistance
Application Question(s):
- Are you able to work full-time, in person in Big Sky, Montana?
- How many years of experience do you have in an operations, office management, HR, or business management role?
- How many years of experience do you have directly supervising or managing employees?
- Which of the following have you personally handled in a professional role? (Select all that apply.)
Recruiting/interviewing
Employee onboarding/offboarding
Payroll or timekeeping
Employee performance issues
Benefits administration
Creating or implementing SOPs
Vendor management
Scheduling/staffing
Bookkeeping/accounting coordination
- Tell us about a position where you were responsible for keeping multiple areas of a business organized and moving forward. What were you responsible for, and approximately how many employees or departments did you support?
- This position regularly requires handling competing priorities—for example, an employee issue, a payroll question, an urgent operational problem, and a request from ownership may arise at the same time. Briefly explain how you would determine what to address first.
- Which best describes the type of work environment in which you perform best?
A highly structured role with clearly defined and consistent responsibilities
A structured role with some changing priorities
A fast-moving small-business environment where priorities change and I may need to work outside my normal responsibilities
I have no preference
- What interested you specifically about this Business Operations & Human Resources Manager position?
Work Location: Hybrid remote in Big Sky, MT 59716
