Role Summary
Wisconsin Getaways and The Castle Vineyard are hiring a Regional Operations & Events Manager to lead property operations and event execution across our portfolio in Sheboygan, Manitowoc, and Brown Counties. This is a dual-role leadership position supporting both our high-end vacation rental operations and our boutique event venue.
Important: To be considered, you must reside within 30 minutes of The Castle Vineyard in Cleveland, WI. This is a hands-on, field-based role requiring regular travel to properties and in-person event leadership.
This role is ideal for someone who thrives in fast-paced environments, enjoys variety, and wants to grow with a luxury hospitality brand.
Core Responsibilities
Vacation Rental Operations (Wisconsin Getaways)
- Serve as the on-the-ground leader for rental properties across your region
- Conduct detailed inspections using Breezeway to verify cleaning, staging, maintenance, and branding
- Resolve guest issues during stays with professionalism and urgency
- Manage local vendors (lawn care, snow, pest, maintenance) and assist internal maintenance team
- Identify performance gaps in cleaner/vendor quality and recommend training or adjustments
- Communicate regularly with homeowners, suggesting improvements that increase satisfaction and bookings
Event & Venue Management (The Castle Vineyard)
- Oversee all aspects of event operations from inquiry to execution and follow-up
- Conduct client tours, book events, and manage scheduling in Hostaway
- Hire, train, and lead part-time event staff for weddings and private events
- Coordinate preferred vendor logistics and maintain venue cleanliness and readiness
- Ensure each event reflects our brand’s luxury and service promise
Sales, Marketing & Growth
- Respond to event inquiries, conduct sales tours, and convert leads into bookings
- Assist with digital marketing campaigns and social media strategy
- Help identify partnership opportunities and community outreach strategies
- Recommend seasonal promotions and business development initiatives
Financial & Strategic Management
- Track event profitability and property performance KPIs
- Monitor vendor costs, stay within budget targets, and flag trends
- Suggest operational improvements that enhance guest experience and profit margins
- Report regularly on inspection scores, maintenance resolution time, and guest reviews
Required Qualifications
- Must live within 30 minutes of The Castle Vineyard (Cleveland, WI)
- 3–5+ years' experience in hospitality, property management, event planning, or operations
- Excellent communication, guest service, and organizational skills
- Tech-savvy: Able to use tools like Hostaway, Breezeway, Google Workspace, and CRM/email platforms
- Valid driver’s license and reliable transportation
- Available on evenings and weekends for events or guest issues
Preferred Qualifications
- Background in boutique vacation rentals or luxury events
- Experience leading teams and managing vendors
- Familiarity with CRM tools and digital marketing strategies
Compensation & Benefits
- Salary range of $70,000–$85,000+ annually, based on experience
- Two weeks of paid vacation
- Long-term growth opportunity within a rapidly scaling brand
- Supportive, entrepreneurial team environment
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About Wisconsin Getaways and The Castle Vineyard
Wisconsin Getaways is the state’s premier luxury and experiential vacation rental management company. We specialize in delivering unforgettable stays by blending top-tier hospitality with operational excellence. With a growing portfolio of high-end properties across scenic destinations, we’re known for our proactive maintenance systems, streamlined workflows, and a team-first culture. Our commitment to both guest satisfaction and process-driven scalability makes us a standout leader in the Midwest vacation rental market.
The Castle Vineyard is a one-of-a-kind luxury estate and event venue nestled in Cleveland, Wisconsin. With its enchanting castle architecture, breathtaking vineyard views, and elevated guest experience, it offers a truly magical setting for weddings, events, and premium getaways. Operated with the same high standards as Wisconsin Getaways, The Castle Vineyard represents the pinnacle of hospitality and aesthetic excellence.
Why Join Us
Working with Wisconsin Getaways and The Castle Vineyard means becoming part of a fast-growing, forward-thinking team that values:
- Innovation – We embrace technology, automation, and AI to streamline operations and deliver exceptional service.
- Growth – With rapid expansion across markets and properties, there are clear pathways for professional development and leadership.
- Impact – Every role directly contributes to memorable guest experiences and operational excellence.
- Culture – We foster a culture of accountability, collaboration, and continual improvement.
Whether you're passionate about hospitality, operations, maintenance, or guest service, this is an exciting opportunity to help shape the future of luxury vacation experiences in Wisconsin.
Job Type: Full-time
Pay: $70,000.00 - $85,000.00 per year
Benefits:
- Flexible schedule
- Paid time off
Application Question(s):
- Do you live within 30 minutes of Cleveland, WI?
- Do you have 3+ years of experience in hospitality or event management?
Work Location: Hybrid remote in Cleveland, WI