Automagically: The Secret Ingredient of Next-Gen Enterprise Software
Back in the 2010s, I spent a ridiculous amount of time trying to set a simple out-of-office reply in an “enterprise-grade” calendar system. One harmless task turned into a multi-tab, multi-manual scavenger hunt. I remember mumbling at the screen like it owed me an apology.
It didn’t. It was just behaving like enterprise software too often does—getting in the way instead of getting out of it.
Now here we are in 2025. AI is everywhere. We’ve got large language models that can write your code, summarize your meetings, and compose jazz. And yet, exporting a basic report from a dashboard still feels like solving a riddle wrapped in a dropdown wrapped in a pop-up you never asked for.
So here’s the question:
If the technology is smarter than ever, why does the enterprise still feel so… clunky?
The Experience We All Want—But Rarely Get
Let’s talk about what we do want.
We want things to work automagically.
It’s that moment when something just clicks—when a system understands your intent without needing explicit instructions. When a vague request returns exactly the right result. When the software quietly fixes your mistake before you even notice it.
- A document syncs where it’s supposed to go.
- A messy spreadsheet turns into usable insights.
- A calendar offers the right time before you ask.
No walkthroughs. No training. No second-guessing.
That’s automagically. And if you’re building enterprise software in this era, it’s no longer a luxury—it’s an expectation.
A Word with Roots—and Respect
Believe it or not, automagically isn’t new. (I heard it used a lot in the 90s when I was at SGI 🙂)
The Oxford English Dictionary dates its earliest use to 1945, and it’s been a mainstay in developer circles since the 1970s. One of the most iconic uses? From Linus Torvalds, creator of Linux, in the official kernel coding style guide:
“…if you want to have linux-c-mode switched on automagically when you edit source files under /usr/src/linux.”
Torvalds didn’t just use the word playfully. He used it deliberately—to describe what good software should do: handle complexity invisibly, while leaving the user in control.
In other words, automagically isn’t cute. It’s a design principle. A goal. A standard.
The Enterprise Is Ripe for Reinvention
Let’s be clear: enterprise software isn’t bad—it’s just burdened.
Burdened by legacy code, by sprawling feature sets, by buyer-driven roadmaps and risk-first thinking. Designed more for procurement than for the people who actually use it.
But that’s also what makes it exciting.
Because when the bar is low, the leap is high.
Modern founders have the chance to reimagine what enterprise software feels like. Not just faster or smarter—but easier, smoother, and surprisingly intuitive.
Enterprise software should stop feeling like a chore and start feeling like a cheat code.
What “Automagically” Means for Engineers and Builders
It’s not just about knowledge workers.
If you’re building for developers, platform teams, or in-house data science groups, automagically still applies—it just looks different.
It’s not about removing complexity. It’s about removing cognitive overhead.
- For engineers, maybe it’s dev environments that spin up with sane defaults and don’t require ten Slack threads to fix.
- For platform teams, it could be observability that surfaces what matters, not what’s available.
- For AI teams, imagine the possibilities of workflows that don’t collapse under the weight of compliance or glue code.
In short: tools that assume you know what you’re doing—and help you do it faster.
The best developer tools feel like they were designed by people who’ve wrestled with the same dragons. They don’t just automate—they anticipate.
The “Automagically” Standard
To deliver this kind of experience, founders should aim for what I’m calling the Automagically Standard. It rests on three pillars:
- Invisible Intelligence
AI should be present but silent. It helps without asking for permission. Think: autocomplete that finishes your sentence—but only when you want it to.
- Zero to Value in Seconds
You don’t get a second chance at first impressions. If your user doesn’t feel progress in under 30 seconds, they’re already forming an exit strategy.
- Failure-Proof Design
Don’t build error messages. Build pathways. When users make mistakes (and they will), meet them with recovery, not friction.
Experience Is the New Moat
In today’s world, AI models are increasingly interchangeable. APIs are table stakes. What’s left?
- Experience.
- Design.
- Delight.
Your moat isn’t what your product can do. It’s how it makes people feel while doing it.
So ask yourself:
- Where are we making users work to get what they want?
- Where are we exposing complexity when we could be offering clarity?
- Where could something happen automagically—and turn a task into a smile?
Because in 2025 and beyond, there are only two kinds of enterprise software:
The kind that works automagically.
Or the kind people stop using.
Just a thought.
P.S. We’ve all felt the power of things that just work. My colleague, Ben Wright, mentioned to me how upgrading from one iPhone to another still feels like magic. His wife swears by Vinted—it’s secondhand shopping that somehow feels first class and “just works.” I still remember using Uber for the first time while living in San Francisco: no learning curve, no thinking, just tap and go, and wow! As my colleague Rav Dhaliwal reminded me, it’s what Arthur C. Clarke meant when he wrote: “Any sufficiently advanced technology is indistinguishable from magic.” Imagine if enterprise software made us feel the same way. Why shouldn’t it?
Other thoughts or ideas about what you’d like to see in the enterprise? Let me know: richard@crane.vc