Building Heritage Brands for the Next Stage of Scale

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.

ALESSANDRO ANDRETTA

ALESSANDRO ANDRETTA

Sales Manager B2B SoEU
  1. You spent almost nine years inside Expedia Group’s ecosystem before joining Prism, a company still shaping its identity in Southern Europe after emerging from Oravel Stays and absorbing distressed inventory like the former Sonder properties. What’s genuinely different about building partnerships for a brand still establishing itself in the region, compared to representing an established marketplace giant?

I think the biggest difference is that, at Expedia, the brand entered the room before you did — and very often the proposition did too.

Customers already knew the company, the marketplace and what Expedia could bring to their business. That allowed you to move very quickly into the actual commercial conversation.

What I find interesting about my current role as Sales Manager at Traum-Ferienwohnungen, part of Prism, is that the situation is more nuanced. Prism — and OYO before it — built much of its European presence through established brands such as Traum-Ferienwohnungen and Belvilla. So you are not starting from zero: these are brands with history, customers and strong recognition in their core markets.

The challenge is taking that heritage and making it work within a broader, evolving commercial organisation.

That makes the role much more entrepreneurial. You cannot assume that what works in Germany will automatically work in Spain, Italy, France or Croatia. You need to understand each market, adapt the proposition, coach the team through more complex conversations and turn what you learn from customers into something actionable for the business.

For me, that combination is probably the most valuable part of the experience. Expedia taught me how to operate at scale. Today, I am learning how to take established brands, adapt them to different markets and build for the next stage of scale.

And in an industry changing as quickly as vacation rentals, I think being able to combine structure with entrepreneurship is becoming increasingly important.

  1. You’re simultaneously Sales Manager for Prism’s vacation rental division and Co-Founder of Canarental in the Canary Islands. Does running your own portfolio change what you ask for when you’re the one selling partnerships to other operators?

Absolutely. Running Canarental means I am also sitting on the other side of the table, and that changes the way I look at partnerships.

When someone pitches me a technology, a distribution channel or a service, I ask very simple questions: Will it bring more bookings? Will it save time? Will it improve the guest experience? And, most importantly, will the numbers actually work?

You become much less impressed by features when you are the one paying the invoice.

That operator perspective has also changed the way I manage sales. I tend to push my team to focus less on what we want to sell and more on what the customer is actually trying to solve.

It also makes me more demanding when we talk about value proposition, ROI or customer experience. Every operational problem eventually becomes someone’s problem, and every promise made during a commercial conversation has to survive contact with the real world.

So yes, running my own portfolio has definitely changed the way I approach commercial leadership. It gives me a much clearer view of the owner mindset and, I think, helps me coach my team to have better, more relevant conversations with operators.

I know what it feels like when the person signing the contract is also the person who has to make the numbers work.

  1. Your Expedia track record shows real, measurable event ROI – a 34% year-on-year increase, 25% ROI on hosted events. In a market where every vacation rental conference now claims to be “essential,” what’s your honest read on which partnership and event investments actually move revenue versus which ones just generate good photos?

Not every “must-attend” event is actually a must-attend event. For me, the question is very simple: did it create qualified pipeline, accelerate existing opportunities, or open doors we could not have opened otherwise?

A busy stand can look great, but a full stand is not the same thing as a full pipeline.

The events that really work are the ones where the audience is relevant and the networking is intentional. You know who you want to meet before you arrive, you prepare properly, and you have a clear plan for what happens afterwards. The best events start before the event and finish weeks after it.

That is actually one of the things I appreciate about VRWS. It has managed to stay very focused on the vacation rental community, and formats like the roundtables and pre-arranged meetings make it easier to have real conversations rather than simply collecting badges and business cards.

We need to be honest about the role of each event. Some are excellent for direct revenue, some for strategic partnerships, some for positioning. The mistake is pretending they all do everything.

I also think we need to be realistic about what “ROI” means. Not every valuable event produces a signed contract the following week. Sometimes the return is a strategic relationship, access to the right decision-maker or accelerating a deal that was already in the pipeline. But you need to know what you are trying to achieve before you spend the money.

I don’t ask whether an event was busy. I ask whether it moved the business forward.

Great photos are nice. Revenue is nicer.

  1. You’re a certified dog trainer alongside your sales certifications, an unusual pairing. Has anything from reading animal behavior actually carried over into how you read a room or a negotiation?

More than I expected, actually.

Dog training teaches you to observe before you react. You learn to pay attention to body language, hesitation, stress, confidence, and all the small signals that tell you much more than words alone.

Dogs are usually more honest than people in meetings, which helps.

In a negotiation or even in a team discussion, I tend to look for the same things: when someone is genuinely engaged, when they are uncomfortable, when they need more information, or when pushing harder is probably the worst possible strategy.

It also taught me something very simple about behaviour: pressure is not the same as motivation, and consistency usually works better than intensity.

Of course, I am not comparing customers or colleagues to dogs — that would probably be a very short career — but the habit of observing first, understanding what is driving the behaviour, and adapting your approach definitely carries over.

So yes, surprisingly, dog training has probably made me better at reading a room.


You’ll have the opportunity to meet Alessandro directly at VRWS

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