At GuestyVal 2025, industry leaders gathered to tackle a challenge that plagues property managers across the vacation rental sector: technology underutilization. The panel, moderated by Yoav Tourel from Guesty, brought together Breezeway CEO Jeremy Gall, Jean-Paul Godfroy, founder and CEO of HUSWELL and Tidy, and Dawn Yeskulsky, CEO and founder of PMS Pros. Together, they broke down how operators can extract more value from their existing tech stacks.
Watch the full session here.
The 40% problem
According to Dawn Yeskulsky, whose firm evaluates property managers’ technology stacks, most operators are barely scratching the surface of their software capabilities.
“Most property managers only use about forty percent of what their technology is capable of doing, and a lot of property managers will have technology that has been in their tech stack for years, and they’re not keeping up with what’s been added,” she said.
This underutilization stems from a common pattern: property managers implement new systems, receive initial training, and then fail to stay current as their providers roll out updates and new features. The result? Frustration, wasted investment, and a misplaced belief that they’ve outgrown their current solutions.
A sophisticated platform takes time to master
The panelists were unanimous in their advice: resist the temptation of shiny new tools. Jean-Paul Godfroy, who manages over 500 properties through Tidy while running HUSWELL as a European hosting platform, emphasized the rapid pace of change in the industry. With platforms like Guesty constantly evolving and adding capabilities, he urged property managers to conduct deep dives into what their systems can already do before considering additions to their tech stack.
The strategy is straightforward: reach out to your customer success teams and account managers. Ask them to show you how to unlock more of your platform’s potential. With comprehensive systems that offer extensive features and integrations, the challenge isn’t capability—it’s fully leveraging what’s already available. Only after mastering your core platform should you look at additional specialized tools.
The emotional decision trap
Drawing a parallel to personal relationships, Yeskulsky described how property managers sometimes make emotional decisions about switching platforms after frustrating experiences with their current systems, dubbing it “rebound technology.”
When PMS Pros receives requests to help find new technology, they first ask why. Often, they discover that switching isn’t necessary. The current system can meet the operator’s needs with proper implementation, training, or minor additions. This approach prevents costly migrations that disrupt every aspect of a property management business.
The panel recommended that property managers provide ten concrete reasons why their current technology fails to meet their needs before considering a replacement. This exercise often reveals that the problem isn’t the technology itself, but how it’s being used.
AI: Beyond the hype
Artificial intelligence is assuming a bigger role in modern property management. Gall offered a grounded perspective on AI’s practical applications, moving beyond buzzwords to tangible benefits.
The key, he said, lies in context and data. The more information you can feed AI systems about your specific properties, business processes, and decision-making criteria, the more effectively these systems can automate administrative tasks. This shifts human resources toward higher-value activities like providing genuine hospitality experiences.
Gall explained that AI is a powerful force in driving automation, though its effectiveness depends on the context and data you can provide. With more information, you can tangibly change how administrative work gets done by shifting the workload rather than replacing humans.
However, the panel acknowledged the tension between automation and maintaining human connection, which is of course a core element of hospitality. Yeskulsky pointed out that guests are becoming increasingly savvy at detecting AI responses, which can feel off-putting in an industry built on personal service.
The solution? Finding the right balance. Automated responses can provide immediate acknowledgment, making guests feel heard, while humans handle the nuanced interactions that build genuine connections. As Gall noted, modern hospitality requires this hybrid approach, where technology enables faster, more efficient service that frees humans to focus on relationship-building.
Deciding when to upgrade
When does it make sense to stick with a good enough tool versus upgrading to something more powerful?
Jean-Paul Godfroy offered clear criteria. Technology should enhance guest experience, improve operational efficiency, or reduce costs. If a tool doesn’t accomplish at least one of these objectives, it shouldn’t be in your stack. He emphasized that software systems aren’t what win new owner contracts or retain guests, but they can significantly impact your bottom line if they’re creating unnecessary complexity.
Yeskulsky added that property managers should demand specificity during vendor evaluations. Vague promises and general assurances are red flags. If a vendor can’t show you exactly how their system accomplishes specific tasks, something isn’t right.
The KPIs that actually matter
Godfroy challenged one of the industry’s favorite metrics: number of listings. According to him, listing count reveals little about business health. “The amount of listings within a portfolio that are actually creating a loss is actually much higher than people would estimate,” he said. Instead, he recommended focusing on three critical KPIs:
- Cost of acquisition (CAC): How much does it cost to acquire a new customer or listing?
- Revenue per available rental (RevPAR) against market: How well does your portfolio perform compared to the broader market?
- Contribution margin per listing: How much profit does each property actually generate?
Understanding these metrics can reveal uncomfortable truths about your business, but they’re essential for making informed decisions about where to invest in technology and operations.
The support factor
An often-overlooked aspect of technology selection emerged during the discussion: post-sale support. Jean-Paul Godfroy emphasized that while every vendor delivers compelling sales presentations, the real test comes when something goes wrong.
Before committing to new software, ask about support channels, response times, and availability. A system that looks perfect during the demo becomes worthless if you can’t get help when you need it. This consideration should carry significant weight in your evaluation process.
Building for scale
For property managers planning to grow, the panel offered guidance on creating resilient tech stacks, to ensure that a system that works for 100 listings could also handle 200 or 300.
The key is avoiding unnecessary complexity. Operators often create multiple workflows when one would suffice, or apply numerous tags when a single tag would work. This over-engineering makes systems fragile and difficult to scale.
Gall cautioned against systems that promise unlimited customization. While flexibility sounds attractive, highly customized solutions become difficult to maintain and can create problems as you grow. Sometimes property managers need to adapt their processes to fit proven software rather than demanding that software bend to accommodate legacy workflows.
Three actionable takeaways
Talk to frontline staff: Before evaluating new technology, speak with everyone in your organization, especially those working directly with guests, handling maintenance, or managing owner relationships. Don’t just consult department heads. The people doing the work every day understand where real improvements can be made.
Master your current tools: Send an email to every account manager for your existing software systems. Ask them to help you achieve maximum value from their platforms. The responses will likely surprise you.
Focus your improvements: Don’t try to optimize everything at once. Each year, identify two or three areas where meaningful improvement will move your business forward. Implementing too many changes simultaneously is a recipe for failure.
The bottom line
The vacation rental industry has become remarkably tech-forward, but technology alone doesn’t guarantee success. The competitive advantage goes to operators who thoughtfully implement and fully utilize their chosen tools, rather than those who simply accumulate the largest tech stack.
In an industry where margins matter and guest experience is everything, maximizing your existing technology investments isn’t just good practice. It’s essential for sustainable growth.
A B2B marketing professional with deep familiarity in the short-term rental industry, translating complex ideas into clear, engaging content. Writes blogs, web copy, and industry reports that inform and inspire. Uncompromising on the Oxford comma.
