Castle Resorts & Hotels is one of Hawaii’s most established hospitality groups, managing hotels, condo-tels, and vacation rentals across the islands and a resort in New Zealand. With nearly 500 staff and a reputation for warm, personal service, they needed a property management system that could handle complexity behind the scenes, without adding friction to the guest experience.

This is the story of how Castle nearly walked away from Maxxton, then came back with a new perspective and a stronger partnership. We sat down with Matt Bailey, President and CEO of Castle Resorts & Hotels to learn more.

The challenge

When Matt Bailey joined Castle Resorts & Hotels in 2023, the team was already midway through replacing Maxxton. “We were in the process of looking for a new property management system” ,he said. “We signed with a company called Track, which is a pure vacation rental solution.”

Implementation began with one of Castle’s vacation rental companies, but the limits became clear right away. “It would be fine for vacation rentals, but it would not work in the hotel space. I learned that in my first week with the company,” Matt said. 

Castle had been with Maxxton since 2014, originally using Newyse, an earlier version of the platform. But in the decade since, that system had never been updated. Over time, Newyse had been customised so heavily to mirror internal processes that it became difficult to modernise. “We had very heavily customised it, and this is a mistake that a lot of companies make. They want software that does exactly what they want, the way they’ve always done it. And that’s not realistic.”

That approach created inefficiencies behind the scenes. “We had a very convoluted manual process where we dumped data out of Newyse into spreadsheets and then manipulated it to fit the formatting of the owner statements,” Matt said. “It was incredibly time-consuming, but it’s the way we’d done things for 30 years.”

Curious to understand what had changed, Matt revisited the recent RFP. “I pulled the RFP that we had just concluded for Track, and Maxxton was the one that came in number two. I started to dig into this and realised that Maxxton had evolved dramatically in ten years.”

Why Maxxton

Castle’s operations don’t fit neatly into a standard hotel or vacation rental model. With three different business types - pure hotels, condo-tels, and vacation rentals, they needed a system flexible enough to manage varied ownership models, guest types, and operational flows.

“One of the things that led us to the RFP process in 2022 and 2023 was a desire to have a single property management system across all accommodation types,” Matt explained. “That’s almost an impossible task because the business models are so different.”

Maxxton had quietly evolved far beyond the version they had originally implemented. “We re-established a dialogue with Maxxton and found that the Maxxton software, which had replaced the Newyse platform, was actually very good and met a lot of our needs.”

Beyond day-to-day bookings, Castle saw a platform that could support broader integration across departments. “Maxxton can take us from the point of presenting your inventory to a prospective guest all the way through to the financial statement,” said Matt. “In particular with condominium owners, vacation rental owners… all the way to their statement.”

That end-to-end capability, paired with adaptability, proved to be the turning point. “Maxxton is the workhorse,” Matt said. “It can adapt to the hotel model or the vacation rental model depending upon where the customer is coming from.”

What stood out even more was the relationship. “Maxxton made some of their strongest resources available to us,” he said. “Maxxton sent people out here. We had a couple of senior Maxxton support people here working with the team.”

“If we were working with Opera or Springer-Miller or some other major PMS system, we wouldn’t be dealing with the people who make policy for the company. We’d be dealing with some salesperson several rungs down. And that makes a big difference.”

The solution

With the decision made, Castle began the process of moving fully onto the updated Maxxton platform.

“We have migrated to Maxxton software almost completely front of the house,” Matt said. “We’re in the process of migrating to the Maxxton software back of the house, which is the owner module, the finance module and so on.”

Castle has also committed to expanding its use of Maxxton’s platform. “We’ve made the commitment that we are going to get to the point where we use Maxxton to its utmost capabilities and eliminate any kind of manual work that can be eliminated.”

As part of that, they’ve recently signed on to implement more advanced modules, including Maxxton’s Revenue Management and Customer Care features. These AI-supported tools will help Castle optimise pricing, automate guest communication, and manage service delivery across departments.

To support the rollout, Castle built a cross-functional stakeholder group. “We put together a relatively large user group that includes operations, finance, marketing, revenue management and brought them into the training realm, had them test the system, understand the system.”

They also created property-level experts to lead adoption on the ground. “It’s very much a train-the-trainer situation,” Matt said. “We create a subject matter expert in various disciplines and also at certain properties, so that they can train new employees.”

“Not everyone participates in every discussion,” he added, “but we have power users at properties… Their representatives participate in the stakeholder meetings and are very familiar with how the system works.”

Communication processes evolved alongside the technology. “We had been using Skype for years, and Skype was just an endless conversation of all kinds of issues that went back 10 years,” said Matt. “We migrated to the Jira ticketing system so that we could keep track of individual issues. They could be assigned to subject matter experts both on both sides, both at Maxxton and here.”

The team is continuing to expand its use of Maxxton modules. “We’re in the process of rolling out housekeeping and maintenance to our teams,” Matt said. “And we regularly discuss how the training is going.”

As Castle looks ahead, technology is seen as a tool to support, not replace, what makes hospitality meaningful. “We are increasingly using technology to create touchpoints with the guest,” Matt explained. “Maxxton provides opportunities to automate guest communication via text, via email.”

But the human element remains central. “Nobody writes to tell you how great the app was,” he said. “They tell you how someone at the front desk went above and beyond and recognised them by name.” Matt continues, “If it gets to the point where do-it-yourself minimises or eliminates personal contact - that’s not my customer.”

When asked how he felt about the relationship today, Matt didn’t hesitate.

“I couldn’t be happier with the way the relationship has evolved… once we got our hands on those other systems, we realised what we had was better than anything we were looking at.”

Results

The collaboration between Castle and Maxxton has led to stronger alignment across teams, more efficient operations, and renewed confidence in the platform’s long-term potential.

• The team has cut out manual, error-prone processes in finance and operations.
  
  
• Staff at the front desk and in reservations prefer Maxxton’s modern interface and usability.
  
  
• A clear internal structure for training, adoption, and feedback has improved buy-in across departments.
  
  
• Maxxton now powers all of Castle’s condo-tel properties and is under consideration for more.