Vadym Klymov is using AI to help you find the hotel for your needs

In this episode of the Everything AI in Travel podcast, I speak with Vadym Klymov, founder and CEO of WinWin Travel, about using AI to solve one of travel’s surprisingly stubborn problems: personalization.

Vadym comes at the problem from firsthand experience. He spent 12 years in hospitality in Ukraine, growing from renting out his grandparents’ four-room summer house to operating his own 48-room guesthouse and working with a 98-room hotel. He was preparing to develop a 300-room property when the war changed everything, and he relocated to the Netherlands.

That eventually led to WinWin Travel.

The premise is simple: Booking.com, Expedia and most hotel websites don't contain enough information to answer the questions that really matter to travellers with specific needs.

We dig into:

🐕 Why travellers with pets can end up calling dozens of hotels just to find somewhere that accepts two large dogs — and determine what it will actually cost

♿ Why accessible travel requires far more detail than an "accessible" checkbox — including bathroom door widths, bed heights, flooring and other specifics

👨‍👩‍👧 Why families, pet owners and travellers with disabilities are WinWin's first three niches — from 38 traveller niches the company has identified

🤖 How WinWin uses AI agents to contact hotels, ask questions, understand free-text responses and turn them into structured, searchable data

📊 Why the company has developed more than 15,000 potential questions for accommodation providers and thousands of corresponding filters

🔄 The surprisingly difficult problem of keeping all that information current — and why simply giving hotels another dashboard to update doesn't work

📧 Why AI-powered email conversations are currently outperforming both forms and AI voice calls for collecting information from busy hotel teams

🔌 How WinWin's MCP strategy could allow other entrepreneurs to build highly specialized travel products on top of its data

🏨 Why WinWin ultimately sees the bigger opportunity as B2B2C infrastructure, rather than simply becoming another niche OTA

🌍 How one LinkedIn post generated hundreds of partnership enquiries from people interested in building niche products using WinWin's MCP

🇦🇪 Why Dubai and the GCC have become a major focus for the company, particularly around accessible tourism

💰 And why Vadym is now actively looking for both niche distribution partners and investors as WinWin expands into the GCC.

One of the most interesting parts of the conversation is how AI changes the interface entirely.

Without AI, extreme personalization could mean confronting travellers with thousands of filters and checkboxes.

With AI, the traveller can simply say:

"I'm travelling to Dubai, I'm a wheelchair user and these are the things I need..."

The AI can translate that natural-language request into the hundreds or thousands of underlying data points required to find accommodation that genuinely fits.

That's a very different version of hotel search — and potentially a much more useful one.

#AI #TravelAI #TravelTech #Hospitality #AccessibleTravel #PetTravel #AIAgents #MCP #HotelTech #TravelStartups #Personalization

Hear the episode here.

In 2026 the podcast is now found on Spotify, Apple Podcasts and now also YouTube (and if you hit subscribe there, you get it before everyone else). You can also catch up on the whole of Series 1 now also fully available in these channels.

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