Strategy for Building Long-Term Owner Relationships
What if near zero owner churn wasn’t just a stretch goal—but a natural outcome of how your company operates?
In Episode 33 of the Property Management Frame Breakers podcast, MasterKey Property Management CEO and Principal Broker, Robert Dell’Osso, sat down with Pablo Gonzalez of Vendoroo to talk about how MasterKey has built a highly retained portfolio of long-term clients.
The full Podcast can be viewed here.
The conversation spans much more than communication. Robert breaks down the systems, leadership choices, and technology investments that make it possible to grow—without sacrificing client trust or service quality.
Below, we’re sharing highlights from the conversation, including short video clips that reveal how MasterKey puts these strategies into practice.
Building Trust from Day One
The foundation of low churn is trust—and according to Robert, that starts with being straightforward from the beginning. Many property managers hesitate to be fully transparent, fearing questions or confusion. At MasterKey, we’ve seen the opposite: the more we share, the more trust we earn—and the fewer problems we face.
Transparency costs nothing, but builds lasting trust →
Clarity Through Financial Reporting
One area where this transparency really pays off is owner reporting. Through AppFolio, our clients have real-time access to cash flow, general ledgers, and other essential reports. Robert discusses how we empower owners to explore their data—and why we welcome questions instead of avoiding them.
“If an owner doesn’t understand something, we explain it—or we bring in our software support team to help. That level of care earns long-term loyalty.”
How transparent reporting strengthens owner confidence →
Proactive, Not Reactive, Communication
It’s not just about numbers. Robert explains how our team communicates around things like inspection results and minor maintenance in a way that adds value—not confusion. Rather than just sending a report, we add our expert recommendations and let owners know what’s already been handled within their approval limits.
What proactive owner updates look like at MasterKey →
Handling Concerns the Right Way
Every property manager faces moments where an owner has concerns—especially around tax season. Robert shares how he personally handles these situations: with calm, clear responses and a willingness to dig into the details. Even when it turns out there’s no real issue, the effort to explain builds trust and strengthens the relationship.
How MasterKey handles owner concerns with care →
Empowering Remote Teams
MasterKey’s success isn’t just about client-facing systems—it’s also about how we build and support our internal team. Robert talks about how we hire and train remote team members with a focus on trust, not surveillance. It’s simple: we treat people like professionals, and they perform like professionals.
Why trust is at the core of our remote team model →
Training, Incentives, and Change Management
As the company has scaled, we’ve invested heavily in onboarding, training, and alignment. From process consultants to regular team check-ins, Robert outlines the infrastructure we’ve built to help every team member succeed. And when the company performs, the team shares in that success through performance-based incentives.
How MasterKey aligns team success with company growth →
Key Takeaways
Reducing churn isn’t about one tactic—it’s about how everything connects. At MasterKey, we’ve created a system where:
Transparency builds trust
Proactive service adds value
Tech supports—not replaces—human connection
Teams are trained and trusted to deliver
Incentives drive retention from the inside out
View the full Podcast Here.
Want to See How It Works?
If you’re a rental property owner in Raleigh, Cary, Durham, or the greater Triangle area and you’re looking for a long-term property management partner, we’d love to connect.
Schedule a call with MasterKey: 919.453.5010
Get a Free Rental Analysis
Call us at 919.453.5010 to talk with a local expert.
MasterKey Property Management | www.masterkeypm.com
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