Understanding the Business Before Selling the Solution
In approaching the 13th edition of the Vacation Rental World Summit, we’re releasing a series of interviews to leaders, key players and highly motivated people in our industry whose companies make a deep impact in our space and will be present at VRWS.
The aim is to get you some insight into these leaders and the company they founded, manage or work for, as well as getting some behind the scenes on their thinking, their motivation and their drive.

Stelios Christakis
1. You originally built Tourmie because you were personally running The Central Boutique Apartments and needed a way to connect guests with local service providers. As Tourmie evolves into Hosperly, you continue to co-run that property management company today alongside leading Hosperly. How do you keep those two roles from pulling product decisions in different directions?
I actually see the two roles as complementary rather than competing.
Running a property management company involves two main areas: day-to-day operations and strategic decision-making. At The Central Boutique Apartments, we have built a strong team that manages the daily operation, which allows me to focus primarily on the strategic side of the business.
That involvement is incredibly valuable for Hosperly because it keeps me close to the realities of property management. I can see first-hand how guest expectations are changing, where teams lose time, where workflows become inefficient and which operational challenges are becoming more important.
But first-hand experience is only the starting point. We do not build Hosperly around the needs of my own property management company. Every product decision goes through broader market validation and product research. We speak with professional property managers across different markets and portfolio sizes, study their workflows and combine their feedback with usage data before deciding what belongs on the roadmap.
So, being involved in The Central Boutique Apartments keeps me close to the problems, while my role at Hosperly is to determine which of those problems are worth solving at scale.
2. Hosperly officially launches just before VRWS in Lyon, right as you reposition from a guest experience app into an AI-powered platform for professional property managers, a space with established players like Guesty and Hostaway already competing hard. What made this the right moment to make that leap, and what is genuinely different about Hosperly’s take on AI compared to what’s already out there?
The leap may look sudden from the outside, but it is the result of years of learning through Tourmie. We started with the guest experience, and the more closely we worked with professional property managers, the more clearly we saw the bigger picture. Guest communication, distribution, reservations, daily operations and guest experience were often spread across different systems. Property managers did not need another isolated feature. They needed a more connected way to run their business.
This feels like the right moment because our understanding of that problem and our ability to solve it have matured at the same time. Years of customer feedback and real-world use through Tourmie have helped us identify the challenges that consistently appear across different markets and property management businesses. At the same time, advances in AI give us new ways to address those challenges at scale. So Hosperly is not a response to the AI trend. It is the natural next step in solving problems our customers have been showing us for years.
We have great respect for established platforms such as Guesty and Hostaway, and naturally there will be overlap in core functionality. But what is different about our perspective is where we started. Tourmie was built around the guest experience, and with Hosperly we are bringing that perspective into the core of property management. Rather than treating the guest journey as a separate layer, we are designing reservations, operations, communication and guest experience to work together from the start.
That foundation also shapes how we think about AI. We do not see it as a standalone assistant or an “AI button” added on top of the software. Its value comes from the context around it: the property, the reservation, the guest, the conversation and the wider operation. That allows AI to support property managers within the workflows where decisions are actually being made, with the goal of making property management more connected, intelligent and proactive.
3. The shift from guest experience app to full platform is a meaningful expansion in scope. What changes concretely for the property managers who already use the product today, once the rebrand and the broader platform go live?
For our existing customers, the immediate priority is continuity, not disruption. Tourmie will continue to operate and be supported while Hosperly is introduced in stages. The Guest App, online check-in, digital guides, service bookings and communication tools they rely on today will remain available. We are not asking anyone to rebuild their operation overnight.
The concrete change is that these guest experience capabilities will gradually become part of a much broader operational environment. Property managers will be able to connect distribution, reservations, communication, daily operations and workflows in one place, all under a single subscription, with AI using the context of each stay across those workflows.
The transition will be carefully managed. As the relevant Hosperly capabilities become available, we will guide customers through the process and make sure the platform supports the way their teams already work.
Hosperly does not discard what we built with Tourmie. It builds around it. What started as a Guest App is becoming the guest-facing layer of a more connected platform for running the entire operation.
4. Before founding the company, you sold telecom and print solutions at Vodafone and Xerox to Greek businesses and public institutions. What from that B2B sales experience shaped how you sell Hosperly to property managers today?
That experience taught me that the most important part of a B2B sale happens before the demo. At Vodafone and Xerox, I was selling complex solutions to organisations with different processes, stakeholders and constraints. You could not begin with technical specifications. You first had to understand how the organisation worked, what problem it was trying to solve and what the cost of doing nothing would be.
That principle has shaped how we sell Tourmie and continues to guide how we bring Hosperly to market. We do not start with AI or a long list of features. We start by asking property managers how their teams operate, where they lose time, where communication breaks down and what becomes more difficult as their portfolios grow. Only then can we show how our technology can reduce manual work, improve control and help them scale more efficiently.
I also learned that the sale does not end when the contract is signed. Even the best technology creates no value if the team does not adopt it. Onboarding, support and long-term trust are therefore part of the sale, not something that comes afterwards.
The technology may have changed, but the principle is the same: understand the business first, solve a real problem and deliver the value you promised.
You’ll have the opportunity to meet Stelios directly at VRWS in Lyon
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