Last Thursday was Sitecore City Tour Chicago, and I’m still working through the follow-ups. What a day.
If you want the full session-by-session rundown, my fellow MVP Rob Reilley already wrote a great one over on Sitecore Runner (link at the bottom). I’m not going to repeat it here. This is more the “how it felt from the stage and the hallway” version.
Our session
I presented “Operationalizing SitecoreAI: Real-World Journeys from United Airlines & Shure” with Jon Price, Charles Hong from United and Rogelio Villanueva from Shure.
This one meant a lot to me because I’ve been part of both of those implementations, supporting Charlie and Rog and their teams along the way. Standing up there next to them, talking about what actually worked (and what took a few tries), was a pretty cool moment. It’s one thing to ship a project. It’s another to hear the client tell a room full of people how it changed the way they work.
The thing I hope people took away: SitecoreAI doesn’t operationalize itself. The wins came from fitting it into workflows people already had, being clear about governance up front, and putting real effort into change management. The technology was honestly the easy part.
The best part: everyone in one place
I’ve said it before and I’ll say it again – the hallway track is the real conference.
Getting to see everyone in one place was great. Customers, partners, Sitecore folks, MVPs, people I usually only talk to on Slack or LinkedIn. I had a ton of amazing conversations and came away with plenty to think about (and a few things I want to write about here).
A few themes kept coming up across the day, in sessions and in conversations:
- AI has to pay for itself. Nobody’s impressed by a demo anymore. People wanted to talk about ROI, governance and getting buy-in.
- Discovery is changing. More and more of the “first visit” is an AI agent, not a person. That changes how we think about content and structure, not just design.
- Migrations aren’t going away. It’s not if you move off XP, it’s how, and agentic tooling is starting to make the “how” a lot less painful.
Room for improvement
If I had one piece of feedback, it’s that the space was a little cramped for the turnout – which is a good problem to have! It says a lot about how much energy there is around Sitecore in Chicago right now. I’d love to see an even bigger room next year.
None of that took away from what was a great day full of amazing conversations and learnings.
Thank you
A huge shout out to the Sitecore team for putting this together, to everyone who came to our session, and especially to Charlie and Rog for being willing to get up there and share their story. And thanks to Jon for steering the ship.
See you all at the next one!
Resources
- Rob Reilley’s recap on Sitecore Runner – #Sitecore City Tour Chicago Style: Real Conversations About SitecoreAI and Digital Transformation: https://sitecorerunner.com/2026/05/08/sitecore-city-tour-chicago-style-real-conversations-about-sitecoreai-and-digital-transformation/
