Customer Story
MasterKey Property Management: Unlocking Growth Through Performance-Driven Tools
MasterKey Property Management
Established: 2016
Location: Raleigh/Durham, North Carolina
Portfolio: Multifamily, Single-Family, Commercial
Units Under Management: 500+
MasterKey Property Management has partnered with AppFolio since day one, using a true performance platform to streamline operations, delight residents and owners, and empower their team. From AI-driven maintenance to centralized tools and seamless onboarding, AppFolio gives Robert, President and CEO of MasterKey Property Management, the confidence and freedom to scale efficiently and grow without compromise.
100%
18% Annually
2016
“The more we can do directly within AppFolio without relying on multiple platforms, the better. Consolidating tools for communication, self-guided showings, and screening makes operations smoother and reduces errors.”
Robert Dell’Osso
President & CEO, MasterKey Property Management, 500+ Units
Growing With Purpose
Real estate has always been a part of Robert’s story. Long before he founded MasterKey Property Management, he took an active role in helping his family manage rental homes and small apartment buildings. This foundation is what shaped how he viewed investing on his own.
Building a corporate career in IT and pursuing real estate on the side, he quickly realized that dedicating himself full-time to real estate was a more sustainable approach. Robert began exploring property management, and his background in IT made him aware of how outdated and inefficient many management processes are. If he was going to go all in, he knew it meant doing it intentionally, with the right systems and structure and the ability to grow without sacrificing performance.
In 2016, he officially launched MasterKey Property Management and adopted AppFolio from day one. What began as a one-person operation has evolved into a team of 10, managing a little over 500 units in the triangle region of North Carolina.
As President and CEO, his day-to-day responsibilities vary, but his focus remains consistent: to build a business that runs smoothly, scales sustainably, and delivers exceptional results.
“The industry has a reputation for old-school, spreadsheet-heavy processes, and with my background, I knew there had to be a more efficient way to manage properties. When I explored the options, AppFolio stood out as the most robust solution.”
Turning Everyday Tasks Into High-Performing Moments
For Robert, performance isn’t just about the numbers; it’s about delivering a better experience for residents, owners, and his team. At its core, performance shows up in everyday moments, such as how quickly a maintenance request is handled, how clearly an owner receives information, and how confidently a team member can work from anywhere.
It’s the reason he partnered with AppFolio early on, and why it continues to be an essential part of MasterKey’s operations:
“My team embraces AppFolio because it means less manual work. With their iPads, they can handle inspections, work orders, and owner communications directly in the field, eliminating the need to return to an office. Things get done faster, and it makes their lives easier.
From the resident’s perspective, the question of ‘Is it easy to submit a maintenance request?’ is ‘Yes’ with AppFolio. There’s a direct correlation between maintenance responsiveness and residents staying longer. Residents expect things to break, and it’s about how quickly you respond that matters.
And from the owner’s perspective, they can access all their data quickly and easily without having to jump through hoops. Their entire portfolio performance is right there in the Owner Portal.”
With the AppFolio Performance Platform as his single source of truth, he’s able to optimize key workflows and keep everything centralized while reducing errors, eliminating manual steps, and ensuring nothing falls through the cracks.
What Real Performance Looks LikeStaying Ahead Means Embracing AI, Not Avoiding It
In an evolving industry, staying ahead means embracing technology, including AI. By not using AI in a strategic way, Robert knows he’s doing a disservice to his business. Having AI and other capabilities directly embedded in AppFolio simplifies workflows, and his team is happier:
“The more we can do within AppFolio instead of juggling multiple platforms, the smoother our operations run. There are fewer logins, fewer systems to track, fewer chances for mistakes, and the team appreciates that.”
The Future of Agentic AI Is Here
Constantly improving business performance means staying curious and always looking for what’s next, what’s better, and what can elevate the experience for everyone. That mindset is what led Robert to attend FUTURE: The Real Estate Conference by AppFolio, where he found a new solution to evolve his business.
“It was my first time attending an AppFolio conference, and it was a great experience! I met other property managers who are true high performers, and seeing how they efficiently run their businesses reassured me that we were making the right decisions. Some of the best value comes from hallway conversations, learning from peers willing to share.
A moment that stood out for me was when the AppFolio Realm-X Maintenance Performer was announced, because we were already looking to improve our maintenance process. What drew me to this solution was the AI component — automatic triaging, self-guided help by AI, and the ability to reduce how many times a vendor had to come out. Seeing the demos sold me because I wanted to do as much as possible within AppFolio without adding another platform, because managing multiple tools can create tension for the team.”
As the industry’s leading agentic AI, the Maintenance Performer is designed to take full ownership of your maintenance operations. It manages everything from work order intake and triage to dispatch and coordination, improving execution as if handled by your best human coordinator.
With the Maintenance Performer, technicians are equipped for success, residents get faster, more personalized support, and your assets are strategically positioned for long-term value.
Experience Realm-X PerformersLong-Term Success With a Platform Built to Last
MasterKey’s decision to partner with AppFolio has never been about chasing the latest trend or the shiny new object. From the very beginning, Robert evaluated multiple platforms (such as Buildium and Propertyware), but the clear choice was AppFolio:
“I felt that AppFolio was the most robust, offering the most features, functionality, and reporting. It was the best platform to scale my business without having to change software down the road.”
Nine years later, that confidence has grown, as he continually sees innovation and enhancements within AppFolio:
“I have 9 years of data in AppFolio, and I see continual enhancements (small and big) multiple times a week. That gives me confidence to stay.”
After years of seeing AppFolio evolve and deliver, Robert committed to a three-year contract extension:
“We signed a three-year renewal with AppFolio on the Plus tier. Normally, I do one-year agreements, but I didn’t hesitate — this time I’m all in. AppFolio isn’t just a software; it’s an absolute, number-one, most critical partner for MasterKey. They’re part of my management team.”
Accelerating Growth From Day One
For Robert, MasterKey’s growth plans and AppFolio’s capabilities are perfectly aligned. With aggressive plans for growth in 2026, Robert is sure that AppFolio can easily accommodate that:
“From the moment I sign a property management agreement, I can get a property added in AppFolio, set up the resident and owner portals, and start managing immediately. There’s no waiting weeks to get up and running.
That speed and performance are critical when you’re trying to add 12 to 15 units a month and aiming for 30% growth.”
AppFolio makes onboarding a seamless, straightforward process, with a dedicated team guiding you every step of the way to ensure a smooth transition and minimal disruption.
Efficiency That Frees You Up
Running on a true performance platform is about smoother operations and unlocking additional time and freedom. With AppFolio’s automation/AI performance tools and the right staff in place, Robert and his team are more self-sufficient, and he can feel comfortable taking a step away without the business skipping a beat.
Looking ahead, the vision is clear: MasterKey Property Management is aiming for 2,000 doors. And Robert knows that growth will be powered by the same partnership that has gotten him this far.
“What I enjoy is being able to travel without having to log in and work the whole time. Investments like the Maintenance Performer, deeper AppFolio adoption, and hiring the right people are all steps toward that.
I’ve also built a relationship with the Customer Success team over the years, and they always treat me like I’m the most important person in the room.”
Robert Dell’Osso
President & CEO, MasterKey Property Management, 500+ Units
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