STR Property Manager

Reports to: Operations Director
Location: Remote (Must have stable, high-speed internet)
Type: Full Time (High availability required, including weekends/off-hours as dictated by business needs)
Salary: Negotiable

Who We Are
Five Oak is a boutique property management company that owns and manages a curated collection of luxury homes across the United States. We are not a massive, faceless corporation; we are a dedicated team that takes immense pride in the assets we own and the experiences we create. We focus on creating smooth operations behind the scenes, partnering with trusted local vendors, and maintaining strong communication to deliver a consistent and elevated service.
We are building a team that thinks like owners. We value radical accountability, proactive decision-making, and the ability to solve complex problems without hand-holding. At Five Oak, every detail matters, and "good enough" is not in our vocabulary.

The Mission: Why We Need You
Let’s be clear: We need an operator, not just a coordinator.
We are looking for someone to take full ownership of our property portfolio from Point A to Point B. We have a suite of advanced tools (including AI support) to help you, but tools don't solve problems—people do.
You will be the "CEO" of your assigned properties. You are responsible for auditing current processes, managing vendor relationships, driving revenue through smart pricing audits, and ensuring that if a guest has a problem, it is solved before they even hang up the phone.

Key Responsibilities

1. End-to-End Property Ownership
Full Accountability: Take total responsibility for the health and performance of the homes. If a toilet runs, a guest complains, or a calendar is blocked incorrectly, you own the resolution. This includes proactive property and regular maintenance.
Proactive Auditing: Regularly audit property listings (photos, descriptions, communication language), pricing strategies, and operational workflows. Don't wait for something to break; fix it before it becomes an issue.
Creative Problem Solving: Use creativity to handle complex guest scenarios or logistical nightmares. We want solutions, not just reports on what went wrong.
Intense attention to detail: ensure all details for all properties are updated. Assign and monitor tasks, identify issues, find solutions, and ensure visibility to the remainder of team. Thoroughly draft, create, audit, and follow operational checklists.
Review optimization: ensure sentiment is good for guests to proactively prevent bad reviews and ensure good ones.

2. KPI Management & Process Optimization
Build & Track KPIs: Develop and maintain Key Performance Indicators (Response Time, Review Scores, Vendor Cost/Performance, Occupancy Rates). You must be comfortable looking at data and explaining why the numbers are moving.
Process Improvement: Constantly review our SOPs. If a process is slow or expensive, rewrite it. If a price looks too low, flag it and adjust it. If we’re paying too much for a vendor, fix it. Don’t just pay the $500 invoice, ask why it was $500.
Tech Utilization: Leverage our AI tools and CRM to automate the mundane, allowing you to focus on high-level hospitality and strategy.
Reporting: Prepare shift or daily reports for internal communication.

3. Guest Experience & Radical Responsiveness
High-Touch Communication: Handle guest complaints with empathy, speed, and authority. Turn a frustrated guest into a 5-star review through quick thinking.
Availability: Hospitality happens 24/7. You must be extremely responsive to urgent issues. A break in communication can ruin a trip; you ensure that never happens.
Quality Control: Monitor guest sentiment and reviews to ensure every stay meets the Five Oak luxury standard.

4. Vendor Management & Logistics
Command the Supply Chain: You don’t just "schedule" cleaners; you manage them. Negotiate rates, audit their work via photos/video, and hold them accountable to our standards. Turnovers must be completed on time, and properties ready for check-in.
Maintenance Coordination: Oversee repairs from the initial work order to final payment. Ensure vendors are paid correctly and jobs are done right the first time.
Inventory & Assets: Track inventory and supplies proactively to prevent shortages, work with vendors on this.

Who You Are
You act like an owner: You treat our money and our homes as if they were your own.
You are data-driven: You understand that feelings don’t scale—metrics do. You are comfortable building scorecards and tracking performance.
You are unshakeable: When a pipe bursts at 2 AM or a guest is unhappy, you don't panic. You execute.
You are tech-forward: You are comfortable with PM software (Guesty, Breezeway, etc.), Slack, SuiteOps, OTAs and AI tools.
You are hospitality focused: These guests are creating memories and can be stressed. You have to treat them as such.
You are articulate: Your written and verbal English is impeccable. You can negotiate with a contractor and soothe an angry VIP guest with equal ease.

Qualifications
Experience: 3+ years in property management, luxury hospitality, or high-level operations.
Skillset: Strong background in creating SOPs, managing vendors, and analyzing pricing/market trends.
Tech: Proficiency in Property Management Software (PMS), OTA platforms (Airbnb, VRBO), and dynamic pricing tools.
Availability: Must be willing to work flexible hours. This is not a strict 9-5; this is a results-based role. Ability to respond off hours when urgent issues arise. Ability to work independently with minimal supervision.

Ready to apply?
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We look forward to your application!