Hey everyone, welcome back to Structured! We're your AI Podcast hosts. I’m Caleb Jensen, and as always, I’m here with Eric Markette. Today, we’re diving into something that sounds dry but, trust me, can make or break your IT budget—Microsoft 365 licensing. Eric, you ever get that feeling where you think you’ve got your software all sorted, and then suddenly, the costs just start creeping up out of nowhere?Oh, absolutely. It’s like, you blink and suddenly you’re paying for features nobody’s even using. And with Jitasa, that’s exactly what happened, right? They were growing fast, but their Microsoft 365 setup just couldn’t keep up. The admin portal only tells you so much, and if you’re just poking around in there or Googling for answers, you’re probably missing something.Yeah, and it’s not just about the money, either. I mean, when you’ve got different departments—finance, HR, the folks in the field—everyone needs something a little different. If you don’t have a handle on that, you end up with people missing tools they need, or worse, paying for stuff that just sits there unused. Actually, this reminds me of my early days at a startup. We thought we were being clever, just buying licenses as we needed them, but by the end of the year, we’d almost doubled our software budget. All because nobody was tracking who needed what. It was a mess.That’s so common. And with Jitasa, they were relying on internal research and the admin portal, but that only gets you so far. The complexity of Microsoft 365 licensing is, well, it’s kind of a beast. You can’t just set it and forget it, especially when you’re growing and everyone’s needs are changing.Exactly. And the risk isn’t just overspending. If you’re not careful, you can end up with access gaps—like, someone in HR can’t get to a tool they need, or you’re missing out on security features. It’s not just an operational headache, it’s a strategic problem. And that’s where Jitasa realized, “Okay, we need some outside help.”Right, so that’s when they brought in Chris McDuffie from Structured. Chris is, I mean, the guy lives and breathes Microsoft 365. He didn’t just look at what they had and say, “Here’s a cookie-cutter fix.” He actually sat down with them, figured out what each department needed, and built a plan that fit their real-world situation.Yeah, and that’s huge. I think a lot of folks underestimate how much value there is in just having someone who knows the licensing landscape inside and out. Chris helped them do a full review—like, not just “Do you have enough licenses?” but “Are you using the right ones? Are you bundling them in a way that makes sense?” It’s like, you wouldn’t buy a sports car for your grandma to drive to the grocery store, right? You match the tool to the job.Exactly. And they didn’t just stop at picking the right licenses. They looked at how to integrate everything smoothly, so the transition didn’t disrupt anyone’s work. Plus, security was a big deal for Jitasa, since they handle a lot of sensitive data. Chris made sure they were covered on that front, too.And the proactive license management piece—tracking usage, right-sizing, making sure you’re not over-purchasing or under-licensing. That’s where a lot of organizations slip up. I mean, what do you think, Eric? If someone’s listening and wondering if their own licensing is a mess, what should they be asking themselves?Good question. I’d say, first, ask: Do you know exactly who’s using what? Are you paying for features nobody touches? Are there people sharing accounts just to save a buck? That’s a compliance nightmare. And are you reviewing your licenses regularly, or did you just set it up once and walk away?Yeah, and don’t forget about training. If your team doesn’t know how to use the tools, you’re not getting your money’s worth. And, uh, I always mess this up—was it miscounting licenses or under-licensing that got that one client in trouble? I think it was both, actually. Anyway, the point is, you gotta keep tabs on it all the time.Totally. And sometimes, just having an outside perspective—someone who’s seen all the weird edge cases—can save you a ton of headaches down the road.So, let’s talk results. After working with Structured, Jitasa ended up saving over $25,000 a year on Microsoft 365 licensing. That’s not pocket change, especially for a nonprofit. But it wasn’t just about the money—they also made IT way more efficient. People got the tools they needed, and the whole system is now set up to scale as they grow.Yeah, and that’s the key. The solution wasn’t just a quick fix—it’s something that’ll keep working as Jitasa keeps expanding. Regular license reviews, making sure employees are trained, and staying flexible as tech changes. That’s what sets you up for long-term success.And it’s not just Jitasa. I know you had a client, Eric, where a regular licensing review actually caught a compliance issue before it turned into a big problem, right?Yeah, exactly. We had a client who thought they were all set, but when we did a deep dive, we found a bunch of users sharing accounts. That could’ve led to some serious compliance fines. We got them sorted out before it became a crisis. It’s one of those things—if you’re not looking, you don’t know what you’re missing.So, if you’re listening and you’re not sure if your Microsoft 365 setup is really working for you, maybe it’s time for a checkup. Don’t wait until you’re bleeding money or scrambling to fix an access issue. And hey, if you’ve got questions, you know where to find us.Yeah, and we’ll be back soon with more stories and tips. Caleb, always a pleasure.Right back at you, Eric. Thanks for tuning in, everyone. This is Structured, your AI podcast hosts signing off—see you next time!

Episodes

Unlocking Microsoft 365 Efficiency