General Manager (Integrator

Destination Willamette is a thriving hospitality company consisting of three core businesses:

Lifestyle Properties Vacation Rentals

Pinot Car Wine Tours

Located in the Willamette Valley, the heart of Oregon’s Wine Country, we’ve built a reputation as the area’s leading destination management company. We offer a curated portfolio of vacation rentals, elevated concierge services, and transportation experiences that rival luxury hospitality standards.

As a locally owned, woman-run business, we pride ourselves on our dynamic team, strong community partnerships, and commitment to delivering exceptional experiences for guests, homeowners, and team members alike.

We prioritize quality, hospitality, and community, creating memorable stays and meaningful connections in one of the most beautiful regions in the country.

We’re looking for a General Manager (Integrator) who can partner closely with our CEO/Founder to turn vision into execution across all three business lines.

This is not a traditional GM role. You will act as the Integrator
, owning day-to-day operations, aligning teams, and ensuring the business runs smoothly, efficiently, and profitably. You’ll bring structure, accountability, and clarity to a fast-growing organization while driving measurable results.

You will lead the team, optimize systems, remove obstacles, and ensure that big-picture goals are translated into actionable plans that get executed. If you thrive on building strong teams, improving processes, and driving performance, this is an opportunity to make a significant impact.

Integrate and align operations across all three entities:
Lifestyle Properties, Pinot Car, and Destination Willamette

Partner with the CEO to execute company vision, priorities, and growth initiatives

Lead day-to-day operations across guest services, housekeeping, maintenance, and admin teams

Build, implement, and optimize systems, processes, and performance metrics

Create accountability across the organization through clear expectations and performance management

Remove obstacles, solve problems, and manage escalations with confidence and professionalism

Oversee budgeting, forecasting, and financial performance across all entities

Strengthen vendor relationships and ensure operational excellence

Enhance employee experience, including benefits, retention, and team development

Serve as the final escalation point for guest and homeowner concerns

Drive strategic growth initiatives and execute key projects

5+ years of experience in Operations, General Management, or similar leadership roles

Proven ability to lead teams, build systems, and drive results in a growing business

Strong organizational and execution skills with a track record of improving operations

Experience working closely with a founder or executive leadership team

Financial acumen including budgeting, forecasting, and performance analysis

Excellent communication and leadership skills

Comfortable addressing challenges, resolving conflict, and making decisions

Proficiency with GSuite and operational systems

Hospitality, vacation rental, or hotel management experience preferred but not required

Bilingual in Spanish is a plus

Compensation: Competitive salary based on experience

Bonus: Performance-based incentives tied to company growth and operational success

Paid time off (PTO, sick days, vacation)

Health, dental, and vision plans (to be enhanced/expanded)

Cell phone stipend

Mileage reimbursement or access to company vehicles

Workplace perks including team activities, food, and flexible scheduling

Relocation Assistance

Schedule: Full-time with required weekend availability, flexibility for evenings and holidays as needed

Location: On-site in Dundee, Oregon area | Relocating to McMinnville late summer 2026