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The latest episode of The Matt & Matt Show is marinated in a bit of tragedy.

We’re sad to report that our dynamic duo could have recorded their latest episode at the hip Manhattan offices of Vimeo.

That’s right: Vimeo. The legendary video platform that’s been a beacon for creators. You couldn’t have asked for a better setup. The lighting was perfect. The sets were sublime. And they had so many cool toys.

But alas… it wasn’t meant to be. At least on this trip.

Truth is, there were too many great conversations at the Boye & Company CMS Experts meeting in New York City last week, hosted at Vimeo’s amazing space. So the Matts dug in, did a bit of impromptu stage work, and returned to their respective sets to cut this conversation.

But don’t fret. They still recorded an episode worthy of your ears, and did it all before heading to Germany for CMS Summit 26. Fortunately, what happened in NYC didn’t stay there: You’ll hear tons of talk about CMS, agentic AI, AEO, and yes – karaoke. It wouldn’t be a New York minute without this group blasting a few tunes together.

The Matts also chat it up about some of the great presentations they saw across the two-day event – from Vimeo’s Sara Benkov to Digitmentor’s Sree Sreenivasan. AI was the through-line, but there was extra-juicy content on a range of topics from diverse speakers. You can read more about the nooks and crannies in these two posts:

More AEO in the spotlight? Pass the mic…

If Episode 4 was about AI agents warming up in the bullpen, Episode 5 puts AI visibility squarely on the mound. And at last week’s New York meetup, Garrepy and McQueeny did their first live, on-stage version of the show, inviting the audience into the conversation and sharing data and research from recent conversations.

Surprisingly (or… not surprisingly?), several digital leaders in the room hadn’t even heard of AEO – Answer Engine Optimization – or weren’t sure how it differed from SEO. As it turns out, Google is still calling the whole shebang “SEO,” which might now encompass “Search Experience Optimization.”

The knowledge gap turned the session into an impromptu “AEO 101,” with the Matts framing it as a wedge opportunity for agencies at a moment when AI visibility has reached the boardroom. McQueeny argued that agencies worried about traditional dev and platform work shrinking should lean into AEO instead of fearing it. There is enormous interest, he said, and leading with AI visibility creates a natural path into new services and ways to redeploy existing teams and talent.

Garrepy played a bit more of the pragmatist, reminding everyone that while SEO evangelized structural and semantic tenets, there has always been a modicum of “smoke and mirrors” to the practice, with monthly retainers and inscrutable reports plaguing ROI. AEO risks falling into the same pattern if enterprises don’t see clear outcomes. Complicating matters: ChatGPT is starting to roll out ads, which is bound to throw the rules of AI search further into flux.

At the same time, Garrepy pointed out that the market is clearly moving. From HubSpot and Conductor to Clutch’s new AI Visibility dashboard, major players are repositioning products explicitly around AI visibility. The real moat, he argued, isn’t the UI – it’s the data corpus that vendors have been quietly building for years. Can this influence the success of AEO? Some vendors say yes, but we'll be watching.

Video and brand equity in the agentic era

Hosting the New York meetup at Vimeo gave the Matts a perfect bridge into the role of video in the AI visibility story – which is a whole lot bigger than most of us realize. For brands trying to control their experience and stand out in AI-powered discovery, Vimeo is reorienting the perception of video as more than a visual accessory. It's a data source that can potentially enhance AI.

The episode also zooms out to the broader identity crisis spreading across the platform ecosystem. Many vendors are no longer content to just be labeled as a CMS, DXP, or CDP. They are re-emerging as AI companies and transforming their brands to follow suit (think SitecoreAI and Umbraco.AI, to name a few). This was recently crystallized by the name change of Treasure Data to Treasure AI, which is now positioning itself as an “Agentic Experience Platform.”

Garrepy notes that this creates real pressure on those vendors to define what their flavor of “agentic system” actually means and where the differentiation exists. With everyone sporting their own agents and orchestration, buyers will be facing more confusion than ever. That’s putting pressure on platforms to square up their messaging and get ultra clear on their value.

‘Build vs Buy’ and the stack evolution

Another recurring theme in this week’s show is the “Build vs Buy” dilemma – a pervasive topic in a world where AI tooling and agentic systems are reshaping the stack.

Matt G. shares stories from enterprises and agencies who are now comfortable saying, “We can build this part ourselves” or “We don’t need that vendor anymore.” With AI-assisted development lowering the barrier to creating and maintaining components, traditional platforms are facing a new reality.

Katie Del Angel, a product designer at Disney who is building a custom CMS for the House of the Mouse, gave an engaging presentation that touched on the opportunities and challenges of standing up a custom solution – one that meets the security and scalability needs of a global enterprise.

Along those same lines, CMS Critic contributors like Geetha Rajan have reflected on the explosion of quickly built, vibe-coded SaaS tools that are bringing serious questions about security, scalability, and long-term ownership. As she proclaims, just because you can ship in days with AI, you still can’t sell to the enterprise. Check out her latest article for a deeper dive.

McQueeny adds a buyer’s-eye view from his interview with Graham Jones of Cytiva, who realized he was responsible for around 50 products – including four separate DAMs. That's a lot. And as vendors race to expand their platforms with AI-accelerated functionality, organizations can drift into accidental redundancy. The takeaway? AI may compress timelines, but governance and clarity are still the goal.

Human stories and embracing a culture of change

For all the AI talk, this episode keeps circling back to people. The Matts spend time reflecting on some storied brands and pivotal leaders – Disney, Pixar, and Bob Iger’s relationship with Steve Jobs – as examples of how the biggest shifts in technology often hinge on human relationships. The duo chat about the power of storytelling and how creative identity, not just product tooling, determines staying power.

Garrepy points to a recent Porsche campaign that proudly emphasized its hand-animated commercial. Viewers didn’t just enjoy the spot – they celebrated the fact that it wasn’t AI-generated. In a world of machine-made content, it feels like the label of “made by humans” has become a strong brand signal.

This ties into a larger theme from the New York meetup and other parts of the ecosystem: the focus on change management and culture. As we heard from multiple voices at the event, some companies and C-level leaders are encouraging their teams to experiment with new tools, share findings, and normalize constant evolution. Without this foundation of innovation, organizations can either cling too tightly to old tools or chaotically chase every AI feature under the sun.

From New York to Frankfurt

Episode 5 also serves as a handoff to the Boye & Company CMS Summit 26 in Frankfurt. And while the New York program featured a rich mix of enterprise, agency, and vendor perspectives – from Manyone to Contentful – Frankfurt delivered an even bigger agenda with more global participants. On the next episode, the Matts will tackle the big takeaways.

Until then, prost! Grab a karaoke mic and sing along. And remember to subscribe on YouTube.

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Matt & Matt meetups

The Matts are on the road! Check out where they’re at – and drop us a line if you’re able to join some of our Boye & Company meetings for CMS Experts and Digital Leaders.

May 18 – Atlanta
CMS Experts/Digital Leaders meetup
May 19 – Atlanta
TYPO3 Summit North America
June 10 – 12 – Copenhagen
Umbraco Codegarden 2026
June 23 – Orlando
CMS Experts/Digital Leaders meetup

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May 20, 2026 – Amsterdam, Netherlands

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CMS Connect 26

August 5-6, 2026 – Montreal, Canada

The best conferences create space for honest, experience-based conversations. Not sales pitches. Not hype. Just thoughtful exchanges between people who spend their days designing, building, running, and evolving digital experiences. CMS Connect brings together people who share real stories from their work and platforms and who are interested in learning from each other on how to make things better. Over two days in Montreal, you can expect practitioner-led talks grounded in experience, conversations about trade-offs, constraints, and decisions, and time to compare notes with peers facing similar challenges. Space is limited for this exclusive event, so book your seats today.

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October 20–21, 2026 – Utrecht, Netherlands

Join us for the first annual edition of our prestigious international conference dedicated to making open source CMS better. This event is already being called the “missing gathering place” for the open source CMS community – an international conference with confirmed participants from Europe and North America. Be part of a friendly mix of digital leaders from notable open source CMS projects, agencies, even a few industry analysts who get together to learn, network, and talk about what really matters when it comes to creating better open source CMS projects right now and for the foreseeable future. Book your tickets today.

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September 30 - October 1, Amsterdam / October 27-28, 2026 – Chicago

Contentstack’s annual customer conference is the premier event for executives, marketing leaders, and developers to redefine their digital experience strategy. This is your opportunity to step out of the "status quo" and into "elite" status, learning exactly how the world’s most successful brands are using the technology you already own to do the impossible. Enjoy a full day of interactive workshops, certifications, and inspirational on-stage sessions designed to help you become an expert on cutting-edge digital strategies and how to turn Contentstack's CMS and adaptive personalization tools into your greatest competitive advantage. Book your seats today.

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Matt & Matt, Episode 5: Karaoke Nights, Live from Vimeo in NYC, and Who Doesn’t Know AEO?