#Sitecore City Tour Chicago Style: Real Conversations About SitecoreAI and Digital Transformation

It was a great experience attending the Sitecore City Tour while representing my new adventure. A spoiler about where I landed is at the end of the blog, but you have to read it all the way through first.

One of the best parts of the event was reconnecting with the Sitecore community. Great presentations around SitecoreAI and digital transformation. I got some great ideas I can bring into my new role. I also met someone who is on a similar journey in the same industry.

Below is a summary of each presentation through both words and pictures.

Welcome Address

Speakers:

  • Dave Tilbury
  • Agata Nowakowska

Summary

The event opened with discussions around Sitecore’s long-term vision, operational scale, and continued investment in AI-driven digital experiences. There was a strong emphasis on helping organizations adapt to rapid change while continuing to modernize customer engagement and content operations.

Nothing like a great start to any event. Agata recently moved to Chicago so we now have another local celebrity here.

A Story About a Lighthouse

Speaker:

  • Dave Michela

Summary

This presentation focused on Sitecore’s long-term product strategy and how organizations can navigate rapid transformation as AI reshapes digital experience platforms. Themes around clarity, direction, openness, unified platforms, and customer partnership were discussed throughout the session. There was also discussion around Sitecore’s ecosystem, marketplace integrations, Microsoft partnership, and the company’s focus areas heading into 2026.This was a great journey on how Sitecore started and where it is headed. Excited to get a glimpse into the future. Did you know the logo was created by a looking down at lighthouse stairs?

Making AI Pay Off: A Candid Conversation on Adoption, ROI, and Governance

Description

Industry leaders share practical insights on moving AI from experimentation to impact, including how organizations prioritize use cases, measure ROI, and establish governance as AI scales across the enterprise.

Summary

This session focused on the practical realities of AI adoption inside enterprise organizations. The discussion centered around governance, ROI, organizational buy-in, and how companies are evaluating whether AI can create measurable operational improvements.

Speakers

Jason Hinton — Director, SE&O – C Services Segment Team, Microsoft

Steven Lamensdorf — CXO, Icreon

Scott Burnell — Global Industry Head, Sitecore

Adeline Ashley — Global Industry Head, Sitecore

A lot of good points on this one. Here are some of the notes I took.

  • It is not just about funding, but if AI can really make things faster.
  • AI needs to be something that helps and does not impact budget.
  • People are more likely to adopt when everyone buys in.
  • There is real pressure of everyone else using AI.
  • There are Governance and transparency concerns in healthcare.
  • Mentioned AI as tool optimizing services in healthcare.
  • Trying to make things look better is not enough.
  • If AI is not embedded in technology, it could be replaced by AI.
  • For healthcare it could increase productivity and help patients.
  • A challenge is how to keep marketer in the loop.
  • A Marketer provides the critical thinking and defines the guard rails.
  • AI is a partner

After the Website: How AI Changes Everything Brands Think They Know About Digital Experience

Description

As AI becomes the experience layer, brands must rethink the role of the website. Learn how discovery, content, and engagement evolve in an AI-driven world — and what leaders must do to stay relevant.

Speaker

Scott Liewehr — Global Vice President, Market Strategy and Growth, SitecoreA lot to unpack here. Here are some of the notes I took.

Summary

This session explored how AI is reshaping discovery, engagement, and the role of the traditional website. As users increasingly turn to AI-powered experiences for research and purchasing decisions, organizations must rethink how they create and structure content.

From my notes:

  • Users start turning to AI for purchases.
  • AI rewards brands that have a point of view.
  • LLM may create too much “fluff” if they don’t know your business.
  • Content audit needs AI visibility dimension.
  • What can I put on a page to get them back to the page from AI?
  • Create content more authentically.
  • Testing content with agents and humans is critical.

Staying Relevant as AI Reshapes How We Discover and Choose

Speakers

  • Carmen Crist — AVP, Marketing Operations, Michigan State University
  • Scott Liewehr — Global Vice President, Market Strategy and Growth, Sitecore

Summary

Michigan State University shared its digital transformation journey and the challenges that came with managing fragmented platforms, inconsistent governance, and growing AI-driven discovery expectations.

This is was really cool to hear how MSU transformed their different CMS sites to Sitecore. They had over 130 sites.

From my notes:

  • Talked about digital journey.
  • Gathered info from other university websites.
  • Dozens of CMS platforms across university.
  • Why transition to Sitecore AIComposable with different technologies? Worked better in their ecosystem.
  • Mentioned the slogan“Next is now” — right thing to do is move forward and not wait.

Operationalizing SitecoreAI: Real-World Journeys from United Airlines & Shure

Speakers

  • Charles Hong — Product Owner, Digital Signage, United Airlines
  • Rogelio Villanueva — Director of Global Web Marketing, Shure
  • Jon Price — Vice President of Sitecore Practice, Americaneagle.com
  • Alex Lentz — Sitecore Solution Architect, Americaneagle.com

Summary

This session focused on how organizations are operationalizing SitecoreAI at scale through workflow integration, governance, and change management. Real-world examples demonstrated how AI can improve efficiency and customer experience when integrated into existing business processes.

Joining an in-house (maybe a spoiler) I really looked forward to this one. Charles and Rog were one of the many Sitecore community members that inspired me to make the change. Hearing from Americaneagle.com is always great because they are huge part of the Chicago market.

From my notes:

  • Journey to Sitecore AI
  • Figma – Showed how this played a role.
  • Marketplace – Custom apps and public apps were impressive.
  • Accessibility – One of the most important things a website must have. Rog made a good point.
  • The Migrator = game changer – This was really cool getting from one CMS to SitecoreAI. I will mention that a lot of partners had a similar tool.

The Migration Game Changer: The Agentic AI Breakthrough for Sustainable SitecoreAI Migrations

Speakers

  • Van Vuong — Director, Digital Platforms, Baylor Scott & White Health
  • Matt Vandermolen — Global Vice President of Digital Experience, Altudo

Summary

This presentation explored how agentic AI can accelerate Sitecore migrations while maintaining scalability, governance, and quality standards. The discussion included real-world healthcare insights and emphasized that organizations should focus less on whether AI-driven migration will happen and more on how to implement it successfully. 

I was really excited about this one. I like to hear from other Healthcare companies (spoiler). Definitely be looking at the their journey and see what I can learn from them.

Some really good takeaways.

  • Not when, but how.
  • Look at other industries for inspiration, not healthcare sites.

Closing Remarks

Speaker:

  • Agata Nowakowska

Summary

The closing remarks reinforced Sitecore’s vision around AI-enabled digital transformation, composable architecture, and operational modernization. The event concluded with a strong focus on innovation, adaptability, and the importance of continuing collaboration within the Sitecore community.

Excited to get started.

Sitecore Community

This is one of my favorite parts of these events. Thanks to Sasha and also my iPhone for various pictures. Dean Winchester snuck in a few of the photos. Fair warning I don’t take the best selfie photos (if you have seen the one with Elijah Wood) you know. Love the views of Chicago from the Willis Tower. Sears if you are old school.

Final Thoughts

The Sitecore City Tour came to me at a great time personally and professionally. I always love connecting with others in my industry and learning new things.

So if you made it this far I wanted to share my badge for this event. Excited about my new adventure starting in June. More to come on LinkedIn.

Essential Tools for the Modern #Sitecore Developer in an AI-Driven World

Several years ago I posted about essential tools for every Sitecore developer. A lot of things have changed since then. You can find that blog here if you want to go down memory lane. Fast forward to the current world of AI. A lot has changed since then, but not just because of AI. As it is inevitable, languages have changed and the way we code has. Here is my list of what I like to use in the current year. Let me know what you would add.

Visual Studio Code

VS Code has taken over a lot of functionality that we used to use with Visual Studio. With React components I have not gone back to using Visual Studio unless it is for MVC. Not only does VS Code work well with development environments it works well with opening text files that I used notes for in the past. It also works well on MacOS and seems to have no limitations.

Microsoft Copilot

If you needed a virtual developer that was a parrot on your shoulder this would be it. Using AI you get so many more features now in your development environment. Inlined code previews and contextual recommendations just to name a few. I believe Cursor has become popular, but I haven’t used that as much yet.

Your Preferred AI

ChatGPT, Claude, Gemini etc… are all battling it out. It is good to have some options to run things by. You will be surprised the different answers you get.

Sitecore Starter Kit

Every great project has to start somewhere. I always suggest starting with the starter kit. It not only benefits your architecture, but if you have any support tickets with Sitecore it will be easier for them to troubleshoot. You can find XM Cloud/SitecoreAI starter kit here.

Storybook

You don’t always have access to test something real time and/or you just want to see if things in theory will work. With Storybook as part of your React solution you can test your components before they are used anywhere else. A good example is if you don’t have access to the Content Hub at the moment and you just need to test if something will work. You can simulate the data and see the expected results.

Sitecore Serialization

Unicorn and TDS were both essential products for classic Sitecore sites. However Sitecore Serialization is the way to go for the smoothest transition to serialize your Sitecore items. It works well and easy to setup.

PowerShell

I can’t count the number of times I needed to use PowerShell. You can use it for so many things. From fixing data, to uploading a big set of images and creating reports. You can use AI to help you write scripts. Of course they should be tested with a small set of data. You can find more about it here.

Accessibility Checker

Having an accessible site is important. There are a lot of tools to use. One of the more popular ones is Siteimprove. Anyone should be able to browse a website no matter their special abilities.

AstroGrep

I may not use this as much as I did in the MVC world, but as your solution grows and serialized items this tool will come in handy still. Searching inside files is key when you need to find that hard to find bug issue. You can find it here.

Sitecore Icon Search

Always use this tool to find the correct icon for the right Sitecore item. You can find it here.

Sitecore Author Toolbox

Must have tool for anyone that uses Sitecore. Many great features with this that will make the user experience better. I like dark mode and rearranging how tabs appear. You can find it here.

Sitecore Community

Saving the best tool for last. I dare you to find a better community that helps each other out. Here is a list of Sitecore community sites to join.

  • Join the Sitecore Slack community. You can find it here.
  • Sitecore Reddit channel has all the latest blogs and news. Find it here.
  • Follow and like Sitecore on LinkedIn. Find it here.
  • Find a local Sitecore meetup group. They also have online ones as well.

Wrapping Up

This list will keep changing, but one thing is for certain. AI is a great tool for developers, but will not replace them. You need to make sure code is clean, scalable, secure and ready for production. Code reviews and thorough developers are needed more than ever. So what tools do you use?

#SitecoreAI Exam: Tips for Helping you Pass #Sitecore

Within the last year I passed the XM Cloud exam. When it was announced that XM Cloud would become SitecoreAI I was wondering if I would need to take the exam again. The answer was yes. Now I will say it was close to the XM Cloud exam, but somewhat different. I believe there were more questions. Here is my quick summary to help you pass. On a side note I did one for the Content Hub exam a few years back. You can find that here.

Use a Sandbox if available.

If you have access to a sandbox go through the steps of creating a SitecoreAI site and setting up a development environment. This will help make things more clear to see the actual process of what is involved. Get a site up and running is key.

Use the exam study guides online documentation.

Sitecore learning has study guides and documentation available that will go over much of what you need to learn for SitecoreAI. Here is a link to check it out. https://doc.sitecore.com/sai/en/developers/sitecoreai/sitecoreai.html

Create your own study guide.

Take notes and make a study guide. Even create your own quiz. If you don’t pass the exam the first time quickly write down what you struggled with and put that in your study guide. Using the link above for SitecoreAI you should be able to come up with a great study guide.

Understand Sitecore basics.

  • Templates how inheritance works and how they are defined.
  • Understand how standard values work and why you should use them.
  • Understand the presentation layer and the difference between SXA and non-SXA sites.

Understand how deployments and archtecture work.

You will need to understand how code goes from your local environment to the cloud. Understanding basic integration and Git hub is important. You are already probably using it, but brush up on CI/CD deployment. The deployment setup for SitecoreAI is different than traditional MVC. Make sure you know environmental variables needed and how new sites are provisioned.

Go through the process of creating a component.

Creating a component is pretty straightforward. Following https://doc.sitecore.com/sai/en/developers/sitecoreai/build-your-first-component.html#create-the-rendering-definition should get you started. This will give you a better idea how SitecoreAI differs from Sitecore MVC.

Serialization

Learn how Sitecore serialization works. Make sure you get to know the parameters needed and why such as path. Look at the starter kit and how that is setup.

Use multiple choice strategies.

This is always better said than done. However you have four answers to choose from. I found at least two answers didn’t make sense. So I tried to eliminate those. The last two you really need to figure out which one the answer should be. Look into the question for help, but also look at other questions that may also give you clues. At the end of the day if you can’t decide, choose the one that makes the most logical sense.

Breathe and Relax.

I am getting better at this. I tend to be nervous going into any test I take. I soon relax as the test goes on. I tend to get a little anxious when I don’t have a clear answer to questions. Just breathing and relaxing really does help. Just don’t breathe too loud because the microphone may pick it up and the exam could get paused.  The answer is there, just reread the question and again make the logical choice.

Conclusion

No matter what happens don’t give up trying. If you fail, learn from it and don’t be worried about taking the exam again. I always recommend taking the training and exam prep offered by Sitecore.