Operations Manager

COMPANY OVERVIEW:

The Destination Willamette family of Lifestyle Properties and PinotCar is growing. We are proud to be the area’s first and only premier vacation rental management company, as well as one of the Willamette Valley’s top transportation services. Over the years, we have established a strong reputation for delivering exceptional, personalized service to both our guests and homeowners.

We believe every member of our team is an ambassador of our brand. That means displaying the highest level of professionalism, hospitality, and friendliness in every interaction with guests, homeowners, and fellow team members. By joining our team, you’ll be part of a company committed to raising the standard of service in our community while continuing to grow and innovate.

POSITION SUMMARY:

The Operations Manager is a pivotal leader responsible for overseeing our Maintenance, Housekeeping, and Property Care teams at Lifestyle Properties. You will also, on occasion, handle operations of our PinotCar business. This role is both strategic and hands-on: ensuring seamless daily operations, developing new systems and processes, resolving escalated issues, and driving long-term growth initiatives.

The ideal candidate is proactive, independent, and thrives in a fast-paced, ever-evolving environment. They take ownership of results, think strategically, and are energized by challenges. A natural problem solver, they lead with initiative, hold others accountable, and deliver high-quality outcomes for homeowners and team members.

RESPONSIBILITIES:

Leadership & Team Oversight

• Supervise and support Housekeeping Manager, Maintenance and Property Care teams in daily operations and larger projects.
• Lead team meetings, set clear expectations, and coach staff to maintain company standards.
• Hold staff accountable with consistent follow-up, mentoring, and training.
• Act as the primary operational leader when senior management is unavailable, including weekends and on-call rotations.

Operations & Scheduling

• Oversee scheduling for field and housekeeping teams using platforms such as Breezeway, Turno, Slack and Google Workspace.
• Adjust deployment in real-time to meet unexpected needs.
• Ensure SOPs, checklists, and operational standards are consistently met and refined.
• Monitor key operational metrics and provide senior leadership with data-driven recommendations.

Property Care & Maintenance

• Direct maintenance operations, including inspections, preventative care, and vendor coordination.
• Troubleshoot escalated property issues and ensure timely resolution.
• Oversee seasonal readiness, vehicle maintenance, hot tub care, and minor landscaping.
• Maintain detailed records of maintenance work orders, costs, and labor hours.

Strategic Growth & Development

• Contribute to long-term planning, including the development of new service departments such as Landscaping. Recommend process improvements that boost efficiency, satisfaction, and profitability.
• Support brand growth through community outreach and industry engagement.

QUALIFICATIONS:

Required:

• 3+ years of leadership experience in hospitality, property management, or vacation rental operations.
• Proven track record managing cross-functional teams (maintenance, housekeeping, property care).
• Hands-on knowledge of maintenance fundamentals such as plumbing, electrical, carpentry, and landscaping basics.
• Strong organizational and scheduling skills with experience using property management and task software (Breezeway, Turno, PMS systems, Google Workspace)
• Excellent communication and problem-solving skills; decisive and confident in fast-paced environments.
• Results-driven leader who thrives under pressure, takes initiative, and enjoys solving complex challenges.
• Valid driver’s license and insurable driving record.

COMPENSATION & BENEFITS:

Compensation:

• Annual Salary + Bonus: $55,000 - $70,000 (On Track Earnings of $80,000 - $85,000 based on meeting company goals)

Benefits:

• Employer match 401(k) retirement plan
• Monthly health stipend
• Company vehicle use for work-related travel
• PTO and professional development opportunities
• Discounts on vacation rentals and Pinot Car Wine Tours
• Opportunity to lead and grow with a premier hospitality company

Job Type: Full-time, with a Thursday–Monday schedule (Tuesdays and Wednesdays off). Weekend availability required.

Job Location: Newberg, Oregon