What immediately stood out during our conversation was Ilan’s mix of technical obsession and relentless focus on user experience. This is someone who isolated himself for months to truly understand the mechanics of large language models before most companies had even worked out what ChatGPT meant for their business. That curiosity now powers Navan’s AI strategy, where conversational interfaces are replacing what Ilan calls the old “forms and tables” model of software interaction.
We explored how Navan’s AI assistant, Ava, is already handling thousands of real-world travel support conversations every day, with customer satisfaction scores that rival those of human agents. During major disruption events like Storm Fern and the Heathrow airport fire, Ava scaled instantly, resolving huge volumes of customer requests without the delays and staffing nightmares that traditionally overwhelm travel providers.
But this conversation goes much deeper than travel. Ilan shared his thoughts on why the software industry is moving toward conversational, context-aware interfaces, why most businesses still misunderstand what agentic AI actually means, and how Navan is building proprietary models trained on its own travel data to outperform larger, generic frontier models. We also discussed trust, hallucinations, AI supervision layers, and why companies must stop treating AI as a magic trick and start measuring it against hard business outcomes.
There is also a fascinating human side to this episode. From building a company through market turbulence, investor skepticism, and geopolitical uncertainty, to challenging accepted thinking since his school days, Ilan’s story reflects the mindset of someone who genuinely believes technology should solve real problems rather than create headlines.
If you have been wondering where AI moves beyond hype and starts delivering measurable operational value, this conversation offers a rare look behind the curtain from someone building these systems at scale every single day.
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