Interview With Matteo Cassese – Business Coach And Keynote Speaker At TravelTech Show 2026

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Matteo Cassese is widely recognised as a keynote speaker, business coach, and leadership strategist who focuses on how organisations must adapt in the era of AI-driven transformation. His work centres on helping executives and companies navigate disruption, uncertainty, and digital change, particularly as agentic AI systems begin reshaping decision-making and operational models. With a background spanning Warner Bros. Pictures, Netflix expansion in Italy, and global consulting engagements, he brings a unique blend of media storytelling, corporate strategy, and behavioural leadership insight. Cassese is often described as a “mythmaker,” using narrative psychology to explain how leaders can rebuild identity and influence in complex systems. His keynote sessions at major platforms such as TravelTech Show, IFA Berlin, and other global conferences explore how AI adoption, legacy system disruption, and organisational agility are redefining competitiveness. He advises enterprises like Netflix, LinkedIn, PwC, Sony, and ING, positioning leadership not as management mechanics but as story-driven transformation under technological pressure, where adaptability becomes the core survival skill.

You argue that what software engineers are experiencing right now is an early warning signal for travel. What exactly are they seeing that travel executives are missing?

Engineers are the canary in the coal mine. They live in the future already, and what they see is unnerving: the machine is brilliant on the peaks and clumsy in the valleys. Researchers call it the jagged frontier. What they mean by that is they recognise AI’s performance and capability can vary across tasks – excelling at some and falling short at others. For example, the same technology when asked to write code is as capable as a PhD academic or developer, yet a second later might not be quite sure Wednesday comes after Tuesday. This creates a sense of insecurity in executives who might ask the question “Is it good enough yet?”. But that’s not the right question. The lesson the travel sector needs to learn from engineering is that the work is changing shape and that new shape is jagged. It is complicated for everyone to profoundly grasp so needs to be approached with due diligence in mind. 

Travel relies heavily on fragmented, legacy systems. How can agentic AI truly transform the industry when the underlying infrastructure is so outdated?

Predictions are hard, especially about the future. But what I can see is that the travel industry finds itself at a crossroads. Right now, legacy system providers are rushing to integrate AI. At the same time, autonomous AI agents are building the missing bridges between the existing infrastructure and expediting execution. But a third possible way forward is disruption. Innovative startups might realise that bypassing legacy systems is the way forward. The future of travel is an uncertain mix of all these three paths.

If AI agents start handling the entire booking process for consumers, how do travel brands protect traditional revenue drivers like upselling, cross-selling, and loyalty programs?

Most of that revenue survives on friction, and the agent removes friction for a living. The seat-anxiety upsell, the insurance scare, the “do you also want a car,” the affiliate links stacked at checkout. A human clicks through those because we’re tired and risk-averse. An agent doesn’t get tired. It will book three refundable flights, hold ten hotels on free cancellation, and quietly let nine go. My AI travel agent will know that personally I would never buy insurance, I have my car waiting for me at the airport, but would also never travel on a middle seat. The upsell, cross-sell and application of loyalty programmes becomes personalised and native and therefore arguably more powerful and profitable.

You’ve mentioned this AI shift is different from past industry shocks. How does agentic AI fundamentally change the internal mechanics of planning and selling travel rather than just speeding them up?

Travel has survived 9/11, the financial crisis, COVID. Those were demand shocks. You wait, demand comes back, the model holds. This one rewrites how demand is funneled into a sale, a booking. The funnel evaporates into a conversation with an AI.

Selling stops being about owning the top of the search results. It becomes about being the thing the agent chooses. But agents are not brand agnostic, as they learn from humans. Building a brand still matters. 

For travel leaders attending the show who prefer a “wait-and-see” approach, what is the immediate risk of delaying their agentic AI strategy?

Wait-and-see feels like the safe bet. It’s the innovator’s dilemma: I want to move, I’m scared of the downside, so I’ll let someone else go first. Then a startup eats your lunch. Here’s the strange part. Only 2% to 8% of travellers are comfortable letting AI book for them today, and 66% wouldn’t trust it. Yet 56% already plan their trips with it. Trust is the gap, and gaps close fast. 20 years ago nobody thought we would consume media on a mobile device. Tomorrow we might wake up and all booking forms and calendar dropdowns might have disappeared.