Property Manager

Property Manager – Field Operations Focus

Shift: 5-day workweek & 2 days off; must be willing to be flexible to business needs

Compensation: 80,168.40 annual salary & Quarterly incentive bonus earnings up to 12% of annual salary

Location:
San Juan Island, WA

This is a hands-on, field-based role with significant time spent across the portfolio conducting property inspections, ensuring compliance and quality standards, identifying maintenance needs, and driving issues to resolution. The ideal candidate is organized, proactive, comfortable with technology, enjoys being active in the field rather than primarily behind a desk, and owns the end-to-end homeowner experience for their assigned portfolio. This role serves as the single point of accountability for property performance, homeowner satisfaction, and operational execution.

The Property Manager owns the end-to-end homeowner experience for their assigned portfolio. This role serves as the single point of accountability for property performance, homeowner satisfaction, and operational execution.

• Serve as the dedicated single point of contact for all homeowner inquiries, concerns, and requests
• Build trusted, long-term relationships rooted in transparency, follow-through, and credibility
• Proactively anticipate risks related to performance, condition, or satisfaction and address them before escalation
• Conduct regular proactive check-ins with homeowners
• Deliver difficult conversations (maintenance issues, damages, policy changes) with clarity, empathy, and solutions

• Confidently discuss property performance, revenue drivers, and market dynamics
• Guide homeowners on pricing strategy, marketing optimization, and improvement investments
• Clearly explain tradeoffs, constraints, and decisions
• Maintain detailed homeowner history, preferences, and risk indicators in CRM

• Identify at-risk homeowners and execute retention plans
• Serve as the homeowner advocate in internal discussions and decision-making

• Own day-to-day operational performance for a portfolio averaging 40-80 units (market dependent)
• Ensure properties meet brand, cleanliness, maintenance, and readiness standards
• Conduct and review inspections; address recurring issues through permanent solutions
• Monitor property condition trends and recommend preventative maintenance

• Coordinate with POD and/or third-parties to resolve issues efficiently
• Own work order outcomes, not just submission or tracking
• Make day-to-day decisions independently
• Monitor and actively manage operational cost per property

• Own inspection strategy and cadence for the assigned portfolio
• Independently schedule and prioritize inspections based on:
  • Owner arrivals and owner usage
  • VIP and high-risk guest arrivals
  • Recent maintenance issues or guest feedback
  • Property complexity, size, and condition
  • Time elapsed since last physical walkthrough
• Ensure each property is physically or virtually inspected on a regular, proactive cadence
• Document inspection findings, trends, and follow-up actions clearly
• Escalate systemic issues for process improvement

• Review guest feedback and address property-specific issues at the root cause
• Ensure compliance with local regulations, HOA requirements, and brand standards

• Partner with Revenue, Marketing, Finance, Onboarding, Compliance, and Maintenance teams to deliver outcomes
• Translate internal recommendations into clear homeowner actions and decisions

• Submit requests following established protocols
• Track open items through resolution
• Provide feedback to teams on process gaps and improvement opportunities

• Demonstrate working knowledge of revenue management principles
• Confidently communicate pricing and performance decisions to homeowners

• Lead homeowner relationship onboarding in partnership with onboarding and…