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Beyond Hype: How AI Is Genuinely Changing the Way We Shop Online with Simon Yencken

AI’s not just out there writing poems and passing law exams - it’s changing the way we fill our shopping carts. But here’s the twist: it’s not the flashiest tools making the biggest difference. It’s the quiet, clever shifts behind the screen - those real, measurable changes in how people discover, browse, and buy.


In this episode, I chat with Simon Yencken, founder of FanPlayer, who cuts through the AI noise to show us exactly how the tech is being used to personalise online shopping, boost performance, and rethink what good eCommerce looks like. Spoiler: it’s not magic. It’s just smart strategy.


From Wall Street to Personalised Shopping Carts

Simon’s background is fascinating. He went from legal partner to general counsel at Reuters, then straight into the heart of Silicon Valley at the height of the dot-com boom. That journey shaped the creation of FanPlayer, a company built on the premise that principles from financial trading - real-time data, segmentation, and analytics - could power the future of online shopping.


Turns out, he was right.


What FanPlayer Actually Does

Put simply, FanPlayer makes websites smarter. At its core, it uses first-party data to deliver real-time personalised experiences to users. Think product recommendations, personalised messages, and even dynamic product rankings - all tailored on the fly. And it’s not just about what's happening on the website. FanPlayer also extends these experiences across messaging platforms and off-site interactions.


Their patented segmentation engine is the backbone of it all. It identifies user behaviour in real time, helping brands show the right product to the right person at exactly the right moment.


AI in Retail: Why It Works (and What Breaks It)

One of the most practical takeaways from our chat was just how detailed and sometimes fragile AI implementations can be. Simon shared a few truths: you can’t just throw AI at a website and hope for results. It needs time to train, a constantly updated product catalogue, and infrastructure to actually show those personalised recommendations in real time.

But when it works, it really works.


FanPlayer’s AI-driven merchandising can recommend not just what goes with the product you’re looking at, but what people like you might also want - even if it’s something you didn’t realise you needed. That’s the true power of AI: going beyond 1+1 to suggest Z.


The Privacy Tightrope: Helpful or Creepy?

Simon didn’t shy away from the elephant in the room: data privacy. As users get more conscious about how their data is used, companies walk a tightrope between helpful and intrusive. FanPlayer tackles this with Privacy ID - a privacy-first, cookie-less solution that still allows businesses to personalise content without tracking identifiable user data.

It’s a reminder that good tech doesn’t just deliver performance - it does it responsibly.


Generative AI vs Rule-Based Systems

We also explored the huge leap from rule-based systems (“If the user likes A, show B”) to generative AI that can identify deeper patterns. Simon compared early eCommerce AI to matching socks; today’s AI is matching lifestyles. The shift isn’t just about technology - it’s about a new way of thinking.


What’s Next for eCommerce AI?

Looking ahead, Simon flagged a few key trends:

  • The rise of the AI-powered personal shopper: Think high-end retail experience delivered digitally to every user.

  • The end of static catalogues: AI now builds dynamic, user-specific lists.

  • The need for real infrastructure: AI isn’t plug-and-play. Real-time data requires backend muscle.


SEO Is Changing Too Fast

One of the most interesting pivots in the episode came when we discussed the shift from search engine optimisation to answer engine optimisation. Platforms like ChatGPT, Gemini and Perplexity are starting to surface products and content through AI summaries, not just search listings.


This means brands will need to think about how their content is interpreted and summarised by AI models, not just how it ranks on Google.


The SaaS Shake-Up

AI is also set to disrupt the way software is sold. The old “pay-per-seat” model is under pressure as AI platforms become more modular and accessible. Simon sees massive change coming here too - with traditional SaaS businesses needing to reinvent themselves or risk becoming obsolete.


Having lived through the dot-com boom, Simon is cautious but optimistic. While there are definitely AI companies that are overhyped and under-delivering, the core technology is solid. And for those building defensible, truly valuable solutions, the future is wide open.


As someone who’s worked in digital marketing for over 15 years, this conversation confirmed what I’ve been feeling for a while: AI is not just another tool - it’s a tectonic shift. But success won’t come from chasing trends. It’ll come from businesses who understand the details, invest in the right infrastructure, and always put the user experience first.


Stay tuned to The AI Grapple for more conversations about how AI is reshaping industries, empowering leaders, and helping us navigate the future of work and innovation.



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