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Margot Schmorak left her role in enterprise strategy to build Hostfully, a property management system now serving over 50,000 vacation rental properties globally.
Her reason? She wanted to work on something where she could actually see the difference she was making, and small businesses felt like the right place to start.
What she didn't expect was to enter an industry on the verge of massive transformation.
In 2015, when Hostfully began, the idea of vertical software for vacation rentals was still new. APIs from Airbnb and Booking.com were just becoming available. Property managers were cobbling together Salesforce and HubSpot to run their operations. The infrastructure simply didn't exist yet.
Hostfully has become one of the leading platforms in the space, and not by accident. It achieved it by focusing relentlessly on solving real problems for real operators.
Here's what Margot has learned about building software for an industry that's still figuring itself out.
When Hostfully started, the short-term rental industry was still considered a "cottage industry." You could list a property on Airbnb, do minimal cleaning, and still get five-star reviews. Guests were just happy to have an alternative to hotels.
That world is gone.
"People are expecting a hotel level of quality in the experience of booking and staying and communicating with a short-term rental," Margot explains. "Everything needs to work perfectly. Property managers need better software, better integrations, they need to open the app and get the information right away and be able to answer a guest query immediately."
The shift happened gradually, then all at once. Around 2016–2018, three things converged:
Hostfully was in the right place at the right time, but that didn't make it easy.
Between 2018 and 2019, it felt like a new property management system launched every week. Trade shows were packed with competitors. Margot remembers thinking: "There's 50 different PMSs here. How are we possibly going to make it through?"
The answer wasn't a brilliant strategy or a killer feature. It was something simpler: "We care a lot about our customers and we care about running a good company," Margot says. "The act of doing Hostfully is very fun for everybody who works here. We really enjoy and love the work. I think that kept us in it."
While competitors burned out or ran out of funding, Hostfully kept building. They became a preferred partner with major OTAs. They secured institutional funding. And slowly, the market consolidated around a handful of leaders, with Hostfully among them.
The lesson? In a crowded market, operational excellence and customer focus matter more than being first or flashiest.
The industry is entering what Margot calls "a more demanding chapter." Guest expectations have fundamentally changed and it's no longer enough to provide a clean space with a lockbox code. Guests now expect:
"A long time ago, people would be delighted to see basic functionality in a PMS, just being excited to see multiple reservations on one calendar," Margot notes. "Now each reservation needs to contain all the detailed information and it needs to interact with all the other data in the property management system perfectly."
AI has accelerated this shift. When guests can get instant, accurate answers from ChatGPT, they expect the same from property managers. The bar keeps rising.
For software companies like Hostfully, this means everything needs to fire on all cylinders. No more "good enough." No more manual workarounds. The system has to work, every time, for every guest.
One of the most common questions property managers face: Should I focus on OTA listings or build my own direct booking site?
Margot's answer is refreshingly pragmatic: both strategies can work, depending on your business model.
The OTA-focused approach works well for managers with a network of properties where brand matters less than consistency and convenience. You're optimizing for volume and operational efficiency.
The direct booking approach makes sense when you want a differentiated brand and are willing to invest in marketing. You'll earn more per reservation (no OTA fees), but you'll need to drive your own traffic.
The biggest mistake? Underestimating how much marketing it takes to make direct bookings work.
"We've seen property managers invest a lot of money into a direct booking site only to find out they have to invest even more money into marketing strategy," Margot explains. "But if you have an engine that works for you, you can attract the right kind of guests to your property, probably a little higher quality, and you get more revenue per reservation."
Hostfully's approach is to support both. They integrate deeply with Airbnb, Vrbo, Booking.com, and Google, while also providing tools for direct bookings.
Here's a surprising fact: Hostfully customers sometimes ask to talk to the AI instead of a human support agent.
Why? "An AI tool is going to be able to ingest new help documentation and new product feature launch information faster than a human," Margot says. "So in some cases, they're going to give a better response."
But this doesn't mean humans are obsolete. At Hostfully, AI handles the volume while humans focus on quality control, training the AI, and handling complex escalations. The AI is essentially the support team at their best: patient, accurate, and never tired.
The same principle applies to guest communications. AI can handle most routine questions using content from digital guidebooks, matching the property manager's tone and style. When something needs a human touch, it escalates. Many guests never know the difference, and that's fine.
AI is only as good as how well you teach it. The team at Hostfully uses content from digital guidebooks to inform automated responses — everything from check-in instructions to local restaurant recommendations. The AI learns the property manager's tone and adapts accordingly.
"We've been really thoughtful about using the content that's in our digital guidebooks to inform the answers that a property manager will want to give, all the way down to the tone they'll be using in conversations with their guests," Margot explains.
The result? Faster responses, more consistent communication, and enabling property managers to focus on the problems that actually need human judgment.
When asked what property managers should be thinking about for the next five years, Margot's answer surprised me: the physical space.
"Software is going to become more and more commoditized," she says. "The physical experience needs to rise with the rest of it."
That means:
On that last point, Margot sees a major opportunity. Right now, travel planning is fragmented. You book your accommodation in one place, research restaurants in another, figure out transportation separately. But AI can coordinate all of this seamlessly.
"Software tools in our industry need to work with that better," Margot says. She's been experimenting with AI-powered itinerary building for family trips, asking the AI to consider nap times, kid-friendly activities, public transportation options, and opening hours all at once.
"It's all structured data," she explains. "AI can look at a Google Places API and know when things are open, is it kid-friendly, is it good for lunch or dinner, what are the hours, how much does it cost, where is it located, can you get there on public transportation. All of that is actually very easy for AI to manage."
The property managers who figure out how to integrate this kind of trip planning into their offering will have a significant advantage.
If Margot could start over, what would she do differently?
These aren't revolutionary insights, but they're the kind of hard-won wisdom that only comes from actually building something over nearly a decade.
What stands out most about Margot's approach is the lack of hype. She's not talking about disruption or being a game-changer. Instead, she's focused on solving real problems for real operators, and doing it in a way that's sustainable for the long term. That means caring about customers, running a good company, and being willing to stick with it when the market gets crowded.
90% of the noise monitoring alerts stop after the first notification because most guests don't realize how loud they are. The same principle applies to building software: most problems aren't dramatic. They're just persistent. And the companies that win are the ones that keep showing up to solve them.
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