Regional General Manager
Wisconsin Getaways | Luxury Vacation Homes
Eastern and Southeastern Wisconsin
www.WisconsinGetaways.com
Base Salary: $75,000 to $85,000 per year
Quarterly Bonus: Up to $300 per assigned property per quarter
Portfolio: 12 to 15 luxury vacation homes
Mileage: Reimbursed for approved travel outside the local county
Help Lead Wisconsin’s Premier Luxury Vacation Rental Brand
Wisconsin Getaways is the clear leader in luxury vacation rentals in Wisconsin.
We manage a curated portfolio of exceptional private vacation homes, including lakefront estates, resort style retreats, entertainment focused homes, and one of a kind properties designed for unforgettable group stays.
Our homes range from approximately $700,000 to $5 million in value and include premium amenities such as indoor pools, hot tubs, saunas, movie theaters, arcades, chef style kitchens, lake access, private acreage, and high end gathering spaces.
Guests choose Wisconsin Getaways for milestone birthdays, family reunions, holidays, executive retreats, weddings, golf trips, and once in a lifetime getaways. They are not simply booking a place to stay. They are trusting us to deliver a premium hospitality experience.
We are hiring a Regional General Manager to lead 12 to 15 of our top luxury vacation homes within an assigned region.
This is one of the most important leadership seats in the company.
Why This Role Exists
Wisconsin Getaways has reached a new stage of growth.
We have added a Director of Hospitality, a Director of Operations, and a growing core team to support our expanding portfolio. Now we are looking for a strong property leader who can take true ownership of a defined region and help us raise the standard even higher.
The right person will not just manage tasks. They will own outcomes.
They will know whether a home is truly guest ready. They will notice details others miss. They will build trust with homeowners. They will hold vendors and team members accountable. They will help prevent guest issues before they happen. They will protect the Wisconsin Getaways brand at the property level every single day.
This role is ideal for someone who has operated in hospitality, hotel management, resort operations, private club management, high end property management, vacation rental management, or another service driven environment where standards matter.
The Opportunity
As Regional General Manager, you will be responsible for the operational performance, homeowner experience, guest satisfaction, and overall property condition of 12 to 15 assigned luxury vacation homes.
You will serve as the primary property leader for your region and work closely with our Director of Operations, Director of Hospitality, guest experience team, maintenance team, cleaning partners, vendors, and homeowners.
You will have support, but you will also have real ownership.
This is a hands on leadership role. It is not a desk only management position. You should be comfortable walking properties, inspecting readiness, following up on maintenance, communicating with homeowners, solving guest issues, and making judgment calls in a fast moving hospitality environment.
What You Will OwnProperty Performance
You will ensure each assigned property is clean, functional, well presented, properly stocked, and ready to deliver a five star guest experience.
Responsibilities include:
- Owning the day to day performance of 12 to 15 luxury vacation homes
- Conducting regular property inspections and quality audits
- Ensuring homes are guest ready before arrival
- Identifying cleanliness, maintenance, stocking, staging, and presentation issues before guests notice them
- Monitoring property level feedback, review trends, maintenance needs, and operational concerns
- Partnering with internal teams to ensure repairs, tasks, and follow ups are completed correctly
- Maintaining high standards across kitchens, bathrooms, bedrooms, outdoor areas, entertainment spaces, garages, amenities, and specialty features
Guest Experience
Our guests often spend thousands of dollars per night. They expect a home that is clean, beautiful, functional, and thoughtfully prepared.
Responsibilities include:
- Supporting a consistent five star guest experience across your assigned portfolio
- Reviewing guest feedback and identifying recurring issues or opportunities for improvement
- Helping resolve guest concerns quickly, calmly, and professionally
- Ensuring each property is prepared for premium stays, special occasions, and high expectations
- Partnering with the hospitality team to improve guest communication, arrival experience, and property specific details
- Protecting the Wisconsin Getaways brand through responsiveness, ownership, and follow through
Homeowner Relationships
Our homeowners trust us with valuable assets. They expect professionalism, clear communication, strong judgment, and results.
Responsibilities include:
- Serving as the primary property relationship leader for homeowners in your assigned portfolio
- Building trust through proactive, clear, and professional communication
- Providing updates on property performance, guest feedback, maintenance needs, and improvement opportunities
- Helping homeowners understand repairs or enhancements that protect guest experience and long term revenue
- Balancing homeowner priorities with Wisconsin Getaways brand standards
- Representing the company with credibility, confidence, and sound judgment
Maintenance and Property Condition
Luxury hospitality requires proactive property care. Small issues become expensive problems when guests are paying premium rates.
Responsibilities include:
- Coordinating with internal maintenance team members and outside vendors
- Prioritizing repairs based on guest impact, urgency, owner expectations, and property performance
- Following up to ensure work is completed correctly and on time
- Identifying recurring maintenance issues and helping implement long term solutions
- Supporting seasonal readiness for peak summer operations, winterization, outdoor spaces, pools, hot tubs, saunas, game rooms, and other amenities
- Recommending improvements that enhance guest experience, reduce recurring issues, and improve property performance
Operational Leadership
This role requires someone who can create order, drive accountability, and raise standards without needing every step handed to them.
Responsibilities include:
- Reinforcing Wisconsin Getaways standards across your assigned region
- Leading through influence with cleaners, maintenance team members, vendors, and internal support teams
- Using company systems to track tasks, property notes, maintenance needs, and quality expectations
- Improving processes where gaps exist
- Communicating clearly with leadership about risks, urgent issues, team performance, and property needs
- Helping the company continue moving from reactive problem solving to proactive operational excellence
What Success Looks Like
A successful Regional General Manager will:
- Take full ownership of 12 to 15 assigned luxury properties
- Build strong, trusted relationships with homeowners
- Maintain strong guest satisfaction and review performance
- Reduce preventable guest issues through better inspection, maintenance, and readiness standards
- Improve consistency across cleaning, presentation, stocking, amenities, and property condition
- Communicate clearly and proactively with leadership, homeowners, vendors, and internal teams
- Help Wisconsin Getaways continue growing without sacrificing quality
- Become the go to leader for their assigned region
Peak Season Expectations
The summer season is our most important operating period.
Between May 1 and August 31, this role requires a high level of engagement, responsiveness, and field presence. During peak season, the Regional General Manager will be highly focused on property readiness, guest arrivals, quality audits, maintenance follow through, homeowner communication, and issue resolution.
This role offers flexibility, but it is not a traditional 9 to 5 position. Occasional evening and weekend responsiveness is expected when guest, homeowner, or property needs require leadership attention.
Who Will Thrive in This Role
You may be a strong fit if you have experience in:
- Hotel or resort operations
- Luxury hospitality
- Private club management
- High end property management
- Rooms division leadership
- Housekeeping or maintenance oversight
- Guest services leadership
- Multi property operations
- Vacation rental management
- Event venue or premium guest experience operations
The strongest candidates will be:
- Detail oriented and highly observant
- Calm under pressure
- Strong communicators
- Comfortable working with high value clients or homeowners
- Capable of holding teams and vendors accountable
- Organized without being rigid
- Hospitality minded and service driven
- Proactive rather than reactive
- Comfortable in a growing company where systems are strong but still evolving
- Motivated by ownership, impact, and building something meaningful
This Role Is Not for Everyone
This is not the right role for someone who wants to manage from behind a desk.
It is not the right role for someone who avoids difficult conversations, waits to be told what to do, overlooks details, or wants a predictable corporate environment.
It is the right role for someone who takes pride in high standards, moves quickly, communicates clearly, and wants their work to have visible impact.
Compensation
Base Salary: $75,000 to $85,000 per year
Quarterly Bonus: Up to $300 per assigned property per quarter based on individual property performance and guest experience outcomes
Quarterly Bonus Potential: Approximately $14,400 to $18,000 annually based on assigned portfolio size and property performance
Assigned Portfolio: Typically 12 to 15 properties within the assigned region
Mileage: Reimbursed for approved travel outside the local county
Why Join Wisconsin Getaways
Wisconsin Getaways is building something rare.
We are not trying to be the biggest vacation rental company in Wisconsin. We are building the best luxury vacation rental brand in the Midwest.
Our properties are exceptional. Our homeowners are invested. Our guests expect the best. Our team is growing. Our standards are rising. And the person who steps into this role will have a direct hand in shaping how we scale.
If you are a hospitality operator, property leader, or service driven manager who wants more ownership, more challenge, and more impact than a traditional hotel or property management role, we would like to meet you.
How to Apply
Ready to lead some of Wisconsin’s most exceptional vacation homes?
Please submit your resume and a brief note sharing why this opportunity interests you and what experience has prepared you to lead a portfolio of luxury vacation homes.
Build the standard. Lead the region. Raise the bar.
Pay: $75,000.00 - $85,000.00 per year
Benefits:
- Flexible schedule
- Paid time off
Application Question(s):
- This is a field-based leadership role overseeing 12 to 15 luxury vacation homes across Eastern and Southeastern Wisconsin. Are you comfortable regularly visiting properties in person, including during peak season?
- Do you have reliable transportation and a valid driver’s license for travel between assigned properties?
- How many years of experience do you have in hospitality, hotel/resort operations, property management, private club management, or a similar service-driven leadership role?
- Briefly describe your experience leading operations, guest experience, housekeeping, maintenance coordination, or property readiness.
- Scenario: A guest is checking into a luxury property at 4:00 p.m. You inspect the home at 2:00 p.m. and find several issues, including a cleaning miss, a broken amenity, and an unresolved maintenance task. What would you do first?
Work Location: Hybrid remote in Sheboygan, WI 53081
