Replicating a Sales Playbook Across Multiple Markets
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.

SIMON ASANGER
- You grew DACH from 80 to over 1,200 clients in two years, then had to build an entirely new international sales hub covering CEE, Benelux and Iberia at the same time. What is the first thing that breaks when you try to replicate a playbook that worked in one region across four culturally and regulatorily different markets at once?
The first thing that breaks is the assumption that what worked in one market will work everywhere. Messaging, buying behavior, and compliance requirements differ. So instead of copying the playbook, I keep the core sales process consistent but localize the execution, for example by working with local partners or agencies, building partnerships with local software providers and putting key integrations in place before entering the market. That lets the team scale without losing relevance in each market.
- Before hospitality tech, you managed key accounts for HARIBO and Liquats Vegetals, selling packaged goods into Metro, Aldi and Lidl. What from negotiating with retail giants at that scale actually translates into selling SaaS to independent hoteliers, who operate at a completely different scale and pace of decision-making?
The hardest school for negotiation is a retail buyer’s office. Procurement teams at Metro, Aldi, Lidl are trained to extract another half-cent from every supplier, every day. Charm doesn’t work in that room. You survive by walking in armed with market numbers, cost breakdowns, and volume data, so there’s no soft spot to push on. You either out-prepare them or you lose margin for good. That’s where you learn the hard sell: fighting for cents with facts, not a training deck.
That discipline is what transfers, not the tactics. Hoteliers move at a slower pace and make decisions more emotionally, but I still walk in with the numbers: occupancy trends, competitor pricing and the actual ROI the tool delivers. Data is what turns “it’s too expensive” into “this pays for itself.” Most SaaS reps show up with a pitch. I show up with a case.
- Smartness has publicly said it is building the first true agentic system for lodging, following the €47 million Series B. Has that ambition already changed what your team is actually pitching in the room, from a pricing tool to something closer to an operating system that acts on the hotel’s behalf, and how do independent operators react to that jump?
The Series B and the “agentic system” ambition are real, but that’s not what I lead with. I ask hoteliers what’s actually broken: occupancy, pricing, or a team too stretched to reprice rooms daily. Sell to the need, not the funding round.
Competition doesn’t scare me. It means there’s a real market. The question is how you stand out in a crowded one. We do it by combining AI with people: the software acts, but there’s always a person the owner can call. Independent operators don’t want to hand their hotel to a black box. They want leverage, with someone accountable behind it.
- Your very first job in this industry was selling flash and winter deals to hotels in DACH for Booking.com back in 2010. Fifteen years later you’re selling to that same kind of hotelier, but now representing the vendor rather than the platform. What has changed most about how they think about revenue and technology in that time?
Nothing’s changed, honestly — it’s the same fight in a new costume and most importantly, hoteliers still trust proof from the property next door more than any sales pitch.
Back in 2010, many feared Booking.com would cannibalize direct bookings and take away control. Then they watched competitors who had joined the platform fill rooms they could not sell on their own. Once someone nearby could show that it worked, the conversation changed. That is still the biggest hurdle in hospitality sales. You first have to get your foot in the door, and then the product has to deliver. After that, the results and referrals do the selling.
What has changed is the strategic question. Hoteliers now understand that OTA commissions can be a marketing investment if the platform brings guests they would not otherwise reach. But they also ask harder questions: What margin remains after commissions and discounts? Are these the right guests? How dependent am I on one channel?
The goal is no longer simply to be on Booking.com, but to build the right channel mix, strengthen direct bookings and avoid relying too heavily on any single platform or software provider.
Revenue management and AI are going through a similar adoption cycle. Hoteliers are conservative by nature, and rightly so. It is their livelihood. But once they see a neighboring hotel use a tool successfully, it becomes credible.
So my job hasn’t really changed since 2010: show results, let the hotel next door that’s booked solid do the convincing, and let referrals do what a cold pitch never could.
You’ll have the opportunity to meet Simon and the Smartness team on Oct 8th
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