Last week I had the privilege of attending the Kentico MVP Summit 2026 at Kentico HQ in Brno, Czech Republic. As always, it was an intense week filled with product discussions, strategic conversations, hands-on workshops and valuable time with people across the Kentico ecosystem.
A few weeks earlier, I attended the Boye & Company CMS Summit in Frankfurt. Many of the themes discussed there resurfaced in Brno. Frankfurt highlighted where our industry is heading. Brno made that future feel much more concrete.
Across both events, the conversation moved beyond AI features and tools. The deeper question was how AI is changing the way organisations learn, coordinate and execute. It increasingly seems that competitive advantages are becoming shorter-lived as new tools and workflows spread rapidly across the industry.
Several sessions and discussions during the week offered different perspectives on that shift.
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Organisations know more than they publish.
Brand guidelines exist. Product knowledge exists. Audience insights exist. Editorial standards exist. Yet when AI generates content, much of that knowledge often remains out of reach.
The challenge is rarely a lack of information. More often, organisations struggle to make their knowledge available where it can be used.
That tension was visible throughout CMS Summit 26, held in May at Frankfurt's Museum für Kommunikation. The event brought together around 100 digital leaders to discuss content management, digital experience, and AI.
One of the highlights was the European CMS Idol competition, where CMS vendors demonstrate their platforms live before an audience of peers and practitioners. Representing Webiny, founder and CEO Sven Al Hamad demonstrated an approach to AI-assisted content creation
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Have you also asked your favourite AI assistant for travel advice?
I did. I asked mine a simple thing: get me from Rovinj to Malaga on 16 June.
The answer was completely wrong.
It gave me a ferry that did not run on that date, a bus to the wrong airport, and a flight from an airport that the bus did not serve. The timings overlapped. The whole thing read like an itinerary. None of it would get me to Spain.
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That statement came up in our Boye Digital Leadership peer group meeting in Hamburg this week.
I wrote it down immediately, partly because it was surprising and partly because it captured something broader. AI is moving from experimentation to operations, and organisations are starting to encounter the practical consequences.
I spent the day listening to peers share what is actually happening inside their organisations. Once again, I was reminded that some of the most useful signals about where digital organisations are heading rarely come from reports, keynotes, or vendor presentations. They emerge through conversations
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The web has a new audience: machines.
AI agents, search assistants, summarisers and retrieval systems are already reading, interpreting and re-presenting what organisations publish. Sometimes they get it right. Sometimes they guess. And when they guess badly, the wrong answer may still carry your brand.
In this member call, we’ll explore Machine Experience — MX — and what it means to design digital content and platforms so machines can read, trust and act on them reliably. The session draws on Tom Cranstoun’s new book….
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I said Atlanta was "HOTlanta," and this group really turned up the heat. We had a packed session at yesterday’s digital experience leaders group meeting, where Matthew McQueeny and I covered everything from the state of martech to the angles of agentic AI, with a through-line focus on open source CMS.
Building on a whirlwind global tour of insights that took us from New York to Frankfurt to the vibrant Poncey-Highland neighborhood of ATL, we were treated to some fantastic perspectives from a diverse international group of attendees.
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Day two in Gotham brought the gravitas at the CMS Experts NYC edition, held at Vimeo’s luxe Manhattan digs.
While AI visibility was still a recurring theme, we were treated to some fascinating and thought provoking presentations that spurred debate on everything from evolving revenue models to the role of AgenticOps.
Here’s what stood out
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In a New York minute, we scaled some skyscraping topics at the Boye & Company CMS Experts meeting in NYC, hosted at the hip offices of Vimeo in Manhattan. Matthew McQueeny joined me for a live rendition of our “Matt & Matt” show on the road, where AEO became a central topic of discussion.
What’s clear is that companies feel the urgency to act on Answer Engine Optimization - but there’s still a lot of confusion about the "what" and "how." From ai12z’s Bill Rogers to VShift’s Eric Feige, we were offered a plurality of insights through the vendor and agency lenses.
A couple of through-lines from day one….
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“I can’t join you in the morning, I have to work.”
“Sorry, I can only join from 5pm.”
I’ve heard versions of this for years.
I’m writing this on a Saturday morning, having travelled to an event I was invited to. Looking around, it brings back a familiar disconnect in how learning is treated across organisations.
In Scandinavia, learning is part of the working day.
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It took me a long time to realise this.
For years, I believed it was all about getting the right people in the room. Find the best speakers, bring together smart participants, and the rest would follow. That still matters. Yet over time, it has become clear that the room itself plays a more active role than we often admit.
The environment shapes the conversation.
You can have capable people, a strong agenda, and a clear purpose. Still, conversations never quite take off.
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What does it actually mean to take responsibility for the digital products we build?
Most teams already care about doing the right thing. The harder part is turning that intent into everyday decisions across design, data, platforms, and governance. Responsibility rarely sits in one place. It shows up in small choices, trade-offs, and blind spots across the entire product lifecycle.
In her work, Antonia Fedder breaks corporate digital responsibility down into seven practical aspects.
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AI agents can still feel like others have already started figuring them out. You hear a few confident stories, see a few hands go up in the room, and suddenly the question shifts from what is this? to am I already behind?
This member call is for anyone who is curious, slightly uneasy, or ready to get more hands-on. It starts from the practical reality of daily work rather than a grand strategy. What happens when you stop waiting to understand everything first and simply begin experimenting?
In this conversation, we’ll explore what it looks like to learn by doing. Chris Weier set out with a simple question rather than a plan to build an AI-powered sales team.
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What does freedom actually feel like when you have it? How do money, time, identity, and purpose shift once the routines of full-time work fall away?
These are questions many people carry long before retirement is near. They are not only practical, but deeply personal, and often left unexplored until the moment of change is already close.
In this member call, Christopher Justice, author of 55 & Out: How to Retire With Life to Spare, joins us for a book launch conversation on what happens when work stops being the main structure around which life is organised.
This is not only a conversation about leaving work. It is about shaping what comes next with more intention. The session will introduce the ideas behind 55 & Out and open up a warm, reflective exchange with space for questions and shared perspectives from the group.
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Digital sovereignty has moved from slogan to strategy. In 2026, it is no longer about abstract positioning, but about deliberate choices in procurement, governance, cost, and collaboration.
Across our government and higher education peer group outside the US, this shift is now visible in day-to-day decisions. The same applies in parts of the private sector, particularly in banking and other regulated industries, where questions of control, risk, and compliance are already shaping technology choices.
The practical challenge is replacing dependency with sustainable control. That does not come from isolation, but from more deliberate procurement and management decisions across platforms, vendors, and internal teams. These choices increasingly involve trade-offs between cost, capability, and control.
In a recent member call, Mathias Bolt Lesniak, Project Ambassador at TYPO3, and Jeffrey “Jam” McGuire, Partner at Open Strategy Partners, explored what it takes to turn principle into practice.
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The conversations shaping the future of the web are shifting.
At CloudFest last month in Germany, with its sheer scale, that shift became easier to see. Two topics stood out across almost every conversation: AI and digital sovereignty.
AI is no longer discussed as experimentation. It is shaping expectations, roadmaps, and investment decisions. At the same time, digital sovereignty is moving from policy discussions into practical concerns about dependency, control, and local alternatives.
This is where attention is, and where budget is flowing.
Yet something more fundamental is emerging. The real change is structural. It is about who controls the systems we depend on, how ecosystems are governed, and where value is created. In open source, initiatives like FAIR point to new ways of organising shared responsibility, and new ways to create and capture value within the ecosystem.
CloudFest was new to me this year, and hard to ignore. The conference takes over an entire theme park
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