Growth, AI and Community in Vacation Rentals

1. You came to Guesty from Fiverr, where you helped scale one of the world’s most recognisable digital marketplaces. Nearly eight years in, what has surprised you most about leading operations in the short-term rental industry compared to a pure digital marketplace, and where do you see the deepest structural similarities between the two?

At Fiverr, the job was simple to describe and hard to execute. Take a fragmented market of individuals trading on instinct and reputation, and build the infrastructure that makes that trust transferable at scale.

Short-term rental felt different from the first week. The stakes here are more personal than I had quite appreciated. A bad project on a digital marketplace is a setback. A bad stay in this industry is somebody’s holiday. The kind of trip a family has been saving for. The week their child has been talking about since March. 

Operators feel that responsibility, and they should. It’s why they obsess over the small details, why they take every review personally, why they know their cleaners by name. Eight years in, this is still what I love most about the industry. The people in it pay attention, and genuinely care.

Both industries are built on the same promise: that you can build a real business around what you love, without needing a funding round or an operations team to do it. The tools and the framework exist so you can focus on what you are most passionate about. At Fiverr, that meant a freelancer could compete on creativity and the quality of their work alone. In vacation rentals, it means hosts can build a hospitality business on the strength of the relationships and experiences they create. 

2. Guesty has made AI a central pillar of its platform, with a dedicated suite that spans guest communication, pricing, and content creation. From an operational standpoint, where are you seeing property managers genuinely benefit from these tools today, and what does meaningful AI adoption look like for an operator in practice?

The number I would start with is 40 to 70 percent. That is how AI adoption among Guesty customers moved in a single year. Our PriceOptimizer alone gives operators around 14.2 percent average lift in booked revenue, and it hands an operator half a day back, every single day. Guest communication and listing content now run quietly in the background, with tasks that once took an afternoon now taking minutes.

What I keep coming back to now is capacity: what operators do with the time AI hands back. That is what separates the ones who keep scaling from the ones who plateau.

Take someone who used to spend the first few hours of every morning triaging guest messages. Those hours are theirs again, and they split them two ways. Part goes back into existing relationships: a call to a top-performing property, a check-in with a guest mid-stay, a small touch that gets talked about a month later. The rest goes into growth, the work that always slipped to next week: nurturing a new owner, building the relationship that wins the next contract, onboarding the next property. The best operators treat that recovered time as the most valuable in their day.

That’s why we built Agent Hub. The shift is from AI that suggests to AI that executes. A coordinated team of AI agents now sits across revenue, communication, operations, finance, marketing, and reviews. They share context in real time, and they are trained on 13 years of real short-term rental operations data. When a guest asks for an early check-in, the agent confirms it, the cleaning schedule adjusts, and the upsell goes out, in one pass. Same team, more capacity for the relationships and decisions that actually require a human. 

What that entails, though, is a shift in how businesses think about their teams. In 2020, ‘hybrid-teams’ meant some people were in the office and some were remote. I think that definition is being rewritten. The hybrid team of the next decade is one where humans and AI work together daily, and the operators who figure that out first will grow faster. Not because AI replaces anyone, but because it frees the people on your team to do the things only they can do. Build the relationships. Make the calls that need judgment. Bring the taste and instinct that no model has. That is where I think property management is heading, and the operators I find most exciting are already thinking this way.

3. Guesty now serves a remarkably wide spectrum of operators, from solo hosts with a single listing to enterprise portfolios of 200 or more properties. How do you approach building a platform that serves such different needs without losing focus, and what does that challenge look like from where you sit as President and COO?

Across the spectrum, operators share a common goal of great guest experiences, the nuances lie in different operational priorities, reflecting their current phase of growth. One needs to be up and running by Friday. The other needs configurable reporting, multi-user permissions, integrations with systems we did not build, and compliance their legal and finance teams will sign off on. 

The way we hold both is by being clear about what connects all operators. A solo host with a single listing and an enterprise running hundreds of properties usually want the same thing, to grow without their tools becoming the ceiling. Guesty scales with that journey, because as a business grows, so does its complexity. The features you need when you are managing a portfolio of hundreds are not the ones you needed at your first ten listings. The platform grows with you, so you are never starting over, just building on what you already have. We don’t just build for the operator in front of us. We build for the one they are trying to become.

What scaling companies teaches you is to build for the business a year ahead of where you sit today. The same logic applies when a property manager chooses a platform. A tool that fits perfectly now but will not fit in twelve months is the wrong tool. We try to hold that same standard on behalf of the operators who are doing exactly that.

4. GuestyVal is coming up in Madrid in September, while Guesty is also sponsoring VRWS in Lyon this year. You’re investing in both your own event and key industry gatherings at the same time. How do the two serve different purposes for Guesty — and what does that dual commitment say about how you think about community building in this industry?

VRWS is one of Europe’s most established vacation rental gatherings.It brings the whole industry into one room: operators, OTAs, regulators, technology partners, and a generation of European businesses building this market into something that lasts. We come to VRWS because we want to be in that room. 

A community only thrives when its members show up for it, and that is what brings us here. We come to give back to an industry we are part of, to compare notes with peers, to help an operator who has been stuck on the same problem for months, to work toward the goals none of us can reach alone. The people in those rooms made this industry what it is, and we want to be among them.

GuestyVal is the other side of that practice. In September, we will bring our customers, partners, and team together in Madrid for three days that are equal parts working sessions and celebrations. We design it as a homecoming. The people who use the platform every day, and the partners who build alongside us, in one place. Many of our most important decisions about what to build next year will come out of those conversations.

One is the wider community we belong to, the other is the one we host, and the dual commitment is the point. You do not get to help build an industry from the outside.