In our recent webinar, Built to Last and to Love: Find Your Perfect Owner Match, we explored what it takes to attract and retain the right homeowners for your vacation rental business.
Hosted by Jared Paglialonga and Austin Taylor, this session provided valuable insights into identifying ideal owners, refining service offerings, and strategically growing your portfolio. If you missed it, here’s a recap of the key takeaways.
Watch the full recording:
Why, When, and How to Switch Software
Jared kicked off the webinar by revisiting a crucial topic from our last session: why, when, and how to switch property management software. The key takeaway? Clearly define what you need before making a switch—because if you don’t know what you’re looking for, no solution will fully meet your expectations. If you’d like to revisit that discussion, a recording is available.
Identifying Your Ideal Owner
One of the most insightful exercises shared was the Owner Pivot Grid, a strategic tool that helps property managers evaluate their homeowner relationships based on two key factors: time investment and revenue contribution. This exercise, recommended at least once or twice a year, offers a sobering yet rewarding perspective on whether certain owners align with your business goals.
Key insights included:
- Time vs. Revenue Balance: Owners who demand excessive time but contribute little revenue may not be worth retaining.
- Operational Feasibility: Factors like location, HOA restrictions, and serviceability play a major role in determining an owner’s long-term viability.
- Growth Strategy: The grid helps not only in assessing current owners but also in targeting similar high-value owners in future marketing efforts.
Defining Your Scope of Services
A common challenge for property managers is saying ‘yes’ to every opportunity, which can lead to unsustainable operations. Jared shared real-world examples of managers in Orlando who found themselves stretched thin, managing tasks beyond their scope, such as paying homeowner bills or scheduling maintenance for properties listed under an owner’s personal Airbnb account.
To build a scalable business, it’s essential to:
- Clearly define service offerings.
- Avoid one-off exceptions that disrupt operational efficiency.
- Standardize contracts to ensure consistency across all owners.
Austin emphasized that not every homeowner is the right fit—just as not every guest is your target audience. Property managers should focus on owners whose needs align with their business model.
Knowing When to Reevaluate Your Portfolio
When should you start evaluating your owner portfolio? While many assume it’s based on unit count (e.g., 25, 50, or 75 units), Jared noted that staffing often dictates this decision. As soon as hiring additional owner services personnel becomes necessary, it’s time to reassess whether all existing properties justify the time and resources they require.
Positioning for Long-Term Success (and Exit Strategy)
Jared closed the session with five ‘million-dollar tips’ for structuring owner agreements to maximize business value and ensure a smooth transition in case of an exit.
One crucial component is the assignment clause, which allows contracts to be transferred in the event of a sale. Without this, property managers may only be compensated for owners who choose to re-sign with the acquiring company. Additionally, ensuring your company is listed as an additional insured on homeowner policies protects your business in the event of disasters like hurricanes or wildfires.
Jared and Austin also discussed exit strategies, advising property managers to evaluate whether they want to scale and sell or grow with the intent to maintain long-term operations. Understanding the true value of a property management business is critical, as is structuring agreements that allow for smooth transitions.
Final Thoughts
This webinar provided actionable strategies to help vacation rental managers identify and attract owners that align with their business model, ensuring sustainable growth. The key takeaway? Not every owner is a good fit—by being intentional in your selection process, you can build a more profitable, scalable, and resilient business.
Interested in taking your business to the next level?