From 2 to 220: The Checkmate Rentals Expansion Story
Learn about Chad’s journey into the world of property management and the strategies that helped him scale efficiently.
In the latest episode of the Hospitable Hosts podcast, we welcome Chad Phillis, Founder and CEO of Checkmate Rentals, a nationwide short-term rental property management company, focused on maximizing revenue for homeowners, optimizing operations, and creating exceptional guest experiences. Chad manages 220 STR properties across the US and uses Hospitable to streamline operations and save time.
Chad shares how he launched Checkmate Rentals during the COVID-19 pandemic to redefine short-term rental management by making their hosts their top priority. He discusses the importance of designing a beautiful rental space that evokes emotion to increase a property’s booking rate and highlights the mistakes hosts make when optimizing their listings. Chad also explores how technology helps minimize the hassles of property management, ensure clear communication with guests, and address security and risk management challenges.
Press Play now to learn about Chad’s journey into the world of property management and the strategies that helped him scale efficiently.
Do you prefer to read the highlights? We’ve got a summary of the key takeaways below.
How Chad Got into Property Management
Chad says he started in the industry back in 2017. When he worked with another property management company, he didn't like many of the things they were doing. And then he realized that other companies were doing the same thing, offering one-size-fits-all solutions to property owners.
“I was getting complaints from hosts about management companies. I started taking notes and decided to start a company that's centered on hosts’ needs.”
The company where he worked didn’t survive the COVID pandemic because it had most of its properties in the New York area, which shut down during COVID. Chad was doing his best to expand them across the country because that was one of his roles. But he ended up losing his job, and he was getting married in a month, so he had no idea what he was going to do.
“What a blessing it was because a handful of the hosts reached out to me and said, Chad, we trust you, and we think you can do a good job. And can you help us? And I was prepared. We started with a couple of properties under management, and now here we are, five and a half years later.”
Currently, Chad and his team manage about 220 properties and use Hospitable to automate various aspects of running the business.
Optimizing Property Listing
It’s not easy to stand out in a highly competitive STR landscape, so Chad shared tips for hosts to optimize their listings and rank higher, attracting potential guests. Here is what Chad recommends:
Invest in professional photos that showcase your property, because you really have no chance of ranking high without them.
Create a detailed description that tells the story of your property and elicits emotions because people buy things based on emotion, not because of logic.
Highlight the amenities you offer that set you apart from your competitors.
Complete your listings and keep them up to date.
Managing Guest Communication
Managing 220 properties means communicating with many guests who may have many questions, so Chad emphasizes the importance of using technology to streamline communication. It helps him deliver quick responses across all those properties 24/7.
Chad points out that having a property management system like Hospitable is crucial to effective communication with guests. “Having automated messages for certain touchpoints throughout the stay saves tons of time,” he underlines. “And we pride ourselves on having an industry-best response time or close to it.”
Chad notes that automated responses are also important for ranking high because OTA sites’ algorithms recognize when hosts respond immediately. So he recommends using automated scheduled messages to confirm bookings, send guests check-in and checkout instructions, etc. He recommends using canned responses for common guest questions, yet he says that making responses “sound human, empathetic, and charismatic is key.”
In addition to guest messaging automation, Chad also has a team that works 24/7 to ensure they can get back to guests at any time of day or night, through messaging or phone calls, to handle more urgent, serious situations that require human interaction. He points out that the team uses AI tools that help ensure fast communication.
“Your new AI messaging really can help, too, right? I still always recommend a human touch. You know, look at the message, edit it, make sure it's right. But AI really helps with spelling, grammar, and everything else. That helps speed up dramatically, and because the AI can be trained on the data of each property.”
Security and Risk Management Challenges
Chad says that vetting is essential for mitigating the risks posed by parties and dealing with squatters, so he likes that Hospitable now allows hosts to request ad hoc guest verification.
He also shares that setting the age limit to 25 works best across their portfolio. “That's going to eliminate most of the people who have the potential for partying,” Chad explains. It’s also important to make sure that guests have verified identities on the platform they're booking on and that they either have good past reviews and no bad ones, or they don't have any reviews at all.
For security purposes, Chad finds it helpful to use smart technologies, such as outdoor security cameras, noise monitoring devices, and smart locks.
Listen to the full episode of the Hospitable Hosts podcast to hear Chad’s inspiring story and get actionable insights.
