As AI agents, Copilot, and chat-based experiences continue to evolve, a familiar question keeps surfacing for IT leaders:
If more work can be done through chat, do enterprise apps still matter?
In this edition of Cloudwell Conversations, we chatted with Troy Palacino, Cloudwell’s Head of Product Development, to delve into how enterprise apps are really evolving, and why purpose-built tools like Calendar Overlay, Staff Directory, and Org Chart continue to play a critical role in providing context, clarity, and scale inside Microsoft 365.
With more than eight years at Cloudwell and a background building complex enterprise systems, Troy brings a grounded, product-led perspective that cuts through the hype.
Kelvin Helmholtz (KH): So, how has the role of enterprise apps changed since you joined Cloudwell?
Troy Palacino (TP): When I first joined Cloudwell, SharePoint Online already existed, but it wasn’t nearly as central as it is now. Once Teams really took off, especially during COVID, SharePoint became the backend for so much of how people collaborate, handling things like files, lists, and structure behind the scenes.
Before Cloudwell, I worked on enterprise applications that were deployed into customer environments and had to integrate with lots of other systems. Those apps were already moving toward being web-based and browser-first, and that trend has really solidified.
So, I don’t see it as a radical shift so much as a continuation. Everything is web-based, deeply integrated, and expected to work seamlessly across devices.
KH: Even with a more mature Microsoft ecosystem, what do enterprise customers still struggle with?
TP: Choosing the right tool for the job.
Microsoft keeps introducing new applications, and some of them are genuinely powerful. Loop is a good example. It’s great for fast, flexible collaboration, jotting ideas down in a meeting or sketching out a process, but it’s not the answer to everything.
We’ve seen situations where something starts in Loop because it’s easy, but over time you realize it needs more structure or a different type of system altogether.
Understanding the problem you’re trying to solve and matching it to the right tool is still a challenge for a lot of organizations.
KH: There’s a lot of talk about AI, Copilot, and agents. What feels real today and what still feels like hype?
TP: One thing that’s very real is AI-driven summarization. Search is a good example. If you’re looking for something like PTO policies or internal documentation, AI can pull together a summary that’s actually relevant instead of sending you through dozens of links.
Where I think there’s still a lot of hype is around fully autonomous agent workflows. You see demos where AI agents handle an entire process with almost no human interaction.
I don’t think we’re quite there yet, and I don’t think people are ready for that level of automation making real-world decisions.
Most people still want to be in the loop.
KH: With all this focus on chat and agents, why do purpose-built apps still matter?
TP: Chat is great for very specific questions — things like “Who does this person report to?” or “Which team are they on?”
What you don’t get is context.
With something like an org chart, the value comes from being able to visually explore the structure. You can see reporting lines, departments, how close someone is to senior leadership, and how teams relate to each other. That bigger picture gets lost in a chat-based experience.
The same applies to staff directories. In chat, you might learn that someone works in development. In a directory, you can see why you should contact them, maybe they work in the same tech stack you do, or they’ve listed expertise that’s directly relevant to the problem you’re trying to solve.
[Editor’s note: Read our blog for more on Why Apps Still Matter in an Agent-First World]
KH: Cloudwell has invested heavily in its core apps. What drove those changes?
TP: Calendar Overlay has been around for a long time, and over the years we’ve expanded it to support more real-world scenarios, things like pulling events from Exchange calendars, SharePoint lists, Planner plans, and iCal feeds, all into a single view.
As that functionality grew, we wanted to step back and optimize the underlying structure so it better reflects how customers are actually using the product today, and so it’s easier for us to keep adding new capabilities in the future.
A big part of that work was identifying common patterns across those different data sources and centralizing that logic, while still allowing for source-specific features where they matter. That also made it much easier for us to align with newer SharePoint Framework capabilities that weren’t practical to adopt before.
The result is a foundation that lets us move faster, whether that’s adding features like category-based filtering across Exchange and SharePoint calendars, or preparing the product to take advantage of future Microsoft platform updates.
KH: What improvements have been made to Staff Directory and Org Chart?
TP: Staff Directory has seen significant improvements around configuration and performance, especially for larger organizations. Once you start getting into environments with thousands of users, API limits and throttling can become a real issue, so we put a lot of work into giving customers ways to configure around those limitations without losing functionality.
Org Chart has evolved quite a bit as well. It used to be fairly static — you’d choose a starting point and how many levels to show.
Now it’s interactive. Users can drill down into reporting lines, move up to see managers, and save personalized views. If there’s a part of the organization you always want expanded, the app remembers that and loads it that way the next time you visit the page.
KH: Many Cloudwell customers operate in regulated environments. How do your apps handle governance and security?
TP: We operate entirely within the Microsoft ecosystem.
Our apps run in the customer’s tenant, are installed through Microsoft-approved app stores, and use Microsoft’s existing identity and security model, things like Graph APIs, tenant permissions, and Entra ID. Aside from license validation, which doesn’t store personal data, everything stays inside their tenant.
We’re essentially leveraging Microsoft’s governance model rather than trying to reinvent it.
KH: Do you see AI agents replacing apps or working alongside them?
TP: I think they’ll work alongside each other.
You might not put together an entire PowerPoint presentation or code an entire product from scratch. You tell an agent what you want, it produces an initial draft on which you can iterate. During each iteration, you can interact with the agent to help with more specific isolated updates.
Essentially agents become an “application assistant”.
KH: If you were advising an IT leader today, what should they look for when evaluating enterprise apps?
TP: Focus on tools that do one thing — and do it really well.
A lot of tools try to be Swiss Army knives, but that usually means none of the individual pieces are particularly great. Identify the problem you’re trying to solve, find a tool that solves that problem well, and don’t get distracted by bells and whistles.
KH: Finally, if you were talking directly to an IT leader reading this, someone dealing with real constraints and real challenges, what would you want them to know?
TP: My personal passion is solving problems. That’s what motivates me.
If someone is struggling with a challenge, whether it’s in their Microsoft 365 environment or just figuring out how to approach a particular problem, I’d encourage them to bring that to us.
At Cloudwell, we really listen to our customers. If there’s an issue, or even just a question, we take it seriously. I want the things we build and the work we do to be genuinely useful, and that only happens if we understand what people are actually dealing with.
So yes, bring us your challenges and we’ll do our best to help.
Let’s solve real problems together
If you’re thinking about how AI, Copilot, and agents fit into your Microsoft 365 environment, and where purpose-built tools still add real value, Cloudwell can help you cut through the noise.
From Org Chart and Staff Directory to Calendar Overlay, our solutions are designed to bring clarity, context, and control to modern workplaces.
Have a challenge you’re trying to solve? Let’s talk.