In the short-term industry today, winning the loyalty game means building relationships where the decision to rebook is already made by the end of the stay. To inspire this level of confidence, operators are investing considerable effort into learning and anticipating their guests’ needs. 

At our recent industry conference, GuestyVal, three industry experts broke down how they’re using customer data to build genuine relationships that turn one-time bookers into repeat customers. The common thread: centering the real needs of guests and letting data show you how to serve them better. 

The cost of ignoring data 

Michelle Marquis, STR strategist and founder of The Marquis Effect, champions guest data as one of the most valuable assets operators can own. But most property managers are sitting on untapped revenue. 

Marquis mentioned a client who had amassed a lot of data from people who inquired but didn’t book – and wasn’t using it. “I asked him, ‘What would happen if your competitor got this data?’ He said it would be terrible because it’s so valuable. I said, ‘But you’re not doing anything with it.’ Point taken.”

While information from past guests is essential, Marquis highly recommends collecting data from prospects who haven’t stayed with you yet. Using tools like SendSquared or Revenate, operators can capture valuable information they can use for remarketing – not just for immediate bookings, but for long-term relationship building. 

Marquis has seen operators increase revenue by at least 10% simply by making outbound calls to people who inquired but didn’t book the first time. “That’s low-hanging fruit,” she said. “They were already looking at your area. They didn’t choose you for whatever reason. Market back to them.” 

Build your website around actual guest behavior, not assumptions

Brandy Canaley, COO of Roami, rebuilt her company’s entire brand and direct booking engine from the ground up. When she and her partners first started Roami, OTAs were the primary marketing engine. Brand identity wasn’t considered critical.

“In the early days, we weren’t really paying attention to repeat guests,” Canaley said. “The OTAs were your marketing engine. Brand was not the thing you needed to stress about.”

That changed. When preparing to announce a Series A funding, Roami underwent a complete rebrand — new name, new feel, new custom website designed to appeal to the modern traveler across markets like New Orleans and South Florida.

But here’s where Canaley thinks most operators go wrong: They build websites based on what they think guests want, not how guests actually use them.

Canaley’s team used a tool called Fullstory (similar tools exist) that tracks every customer journey from the moment they land on your site to the moment they leave. It shows rage clicks, dead clicks, navigation paths — the full picture of how people actually interact with your booking engine.

“We had this enormous Google Sheet with every single thing we wanted to do to the site,” Canaley explained. “We prioritized based on what we thought was important, not what guests thought was important. After implementing Fullstory, we completely rearranged everything because things we thought were super important weren’t even on the list of what people were looking at.”

What they discovered:

1. Guests were rage-clicking in the middle of listing cards, trying to get to property details, but the clickable areas were only specific buttons. The solution: Make the entire listing card clickable.
2. All-in pricing matters. Guests want to see total costs upfront with a date selector dropdown (like OTAs offer), not hunt for fees buried in fine print.
3. Creating guest accounts where travelers can see past and future trips builds a sense of loyalty. “It creates this aspect of ‘I’ve booked with them before, I’m gonna keep booking with them, I already have this account,’” Canaley said.

The takeaway: If you have a direct booking website, implement behavior tracking tools. Stop guessing what guests want and start watching what they actually do. Prioritize your development budget based on real user behavior, not internal assumptions.

Scale consistency without losing your soul

Marianne Heder from Property Management Inc. faces a different challenge: maintaining consistent standards across a franchise network while delivering locally authentic experiences. Her answer is what she calls “the right playbook.”

“You don’t even have to go national,” Heder said. “I’m sure all of you with more than ten properties are experiencing this challenge. How do you keep consistency across those properties? It’s all about running the right playbook. If you’re running the wrong playbook, all you’re doing is scaling chaos.”

According to Heder, data isn’t just analytics dashboards and conversion rates. It’s the intelligence that helps you build operational systems that work at scale.

Heder’s three-step/pillar approach:

Build the playbook with data

Use guest feedback, booking patterns, and operational metrics to understand what actually works.  

Embed the playbook in your systems

PMI partners with Guesty specifically because the platform allows them to standardize processes across thousands of properties through an HQ account structure. 

Let data buy you time for the human touch

The human element matters. Automation and standardization are meant to create space for personalization, not replace it. 

“Data should buy you the time to put your soul into your business,” Heder emphasized. “Guests want to book with you, with your company, with your flavor and your taste. Whatever your niche is, whatever makes you different, infuse that.”

“It takes a human to understand what a human needs,” Heder said. “Something as simple as understanding why someone’s coming—a funeral, a wedding, whatever—and then wowing them by doing something unexpected because you know their context. Doesn’t have to be complex, but it has to be human.” 

The metrics that matter most

When asked what metrics they’d never give up, the panelists revealed different priorities that share a common thread.

Heder prioritizes direct booking percentage above all else. “That tells you the story,” she said. “Are you able to build a relationship where they want to trust you enough to come back and book direct?”

According to Marquis, individual guest preferences and behavior matter most. “Collect data on their stay, on the person themselves, their preferences. Then keep communicating based on what you know about them. You’re not doing email blasts, you’re showing them pictures from their last stay and making relevant offers.”

Canaley focuses on website interaction data. “Some tool that allows you to see exactly how guests are interfacing with your direct site so you can prioritize your budget appropriately and not waste money,” she said.

All three metrics point to the same principle: Understanding individual customer behavior drives better decisions than aggregate statistics.”

The blind spots costing you bookings

OTA guest data collection remains a universal frustration. “We all have frustration with collecting data from guests that book through OTAs,” Canaley said. “It would be great if you could easily get that information through their booking so you can continue to nurture that relationship afterwards.” While OTA terms limit direct data collection, smart operators find ways to build relationships during the stay through branded touchpoints, follow-up communication, and creating reasons for guests to voluntarily share contact information.

Shopping cart abandonment represents what Marquis called a massive missed opportunity. “So many companies do not do cart abandonment marketing. It’s easy to implement, you capture that data for the long term, and it’s easy to then market and get them to book.” Guests who start a booking but don’t complete it have high intent — they are ready to commit. A simple follow-up email sequence can recover significant revenue.

Conversion drop-off points reveal friction that kills bookings. Marquis recommended analyzing “where people are dropping off and how you can increase conversion, but also finding a way to get their email information, even when they don’t complete the booking. Understanding where prospects abandon your booking flow shows exactly where your site fails to convert interested guests.”

Friction in the booking flow can be improved with what Heder called the single most revealing exercise. “Experience what your guests experience,” she said. “Sit down and figure out where in that journey you could be missing out on capturing data.” Going through your own booking process and stay reveals friction points that become invisible when you’re running operations daily.

Data serves people, not the other way around

The through-line in this conversation: Data isn’t the point, customers are. The data you collect should help you understand your market through the numbers and reveal how you can tailor their experiences to best serve their needs. 

The operators building sustainable direct booking businesses aren’t the ones with the most sophisticated analytics dashboards. They’re the ones using simple data to understand what individual guests want, then delivering it consistently.

Guest data is money in the bank, but only if you actually spend it. Learn more about Guesty’s CRM and analytics tools, or consult with a specialist. 

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