Why Enterprise Software Sucks

Enterprise software exists in its own strange, dystopian economy. A parallel universe where the laws of quality, efficiency, and common sense are entirely optional. It’s not just about the software itself; it’s about the bizarre rituals and absurd pricing models that come with it. Let me walk you through the madness.

Step 1: Pay Us to Explain How It Works

First, you don’t just buy enterprise software; you must pay to understand it. It’s not a product. It's an enigma wrapped in a mystery, guarded by consultants in expensive suits.

When you sign up, we don’t just hand you the keys and wish you luck. Oh no, we join your company as “consultants” (for a hefty fee, of course). We hold meetings, host workshops, and prepare glossy slide decks that, ironically, make the software look even more complicated than it actually is. By the end, you might understand how it works,or you might not. But one thing is for sure: you’ve already spent a small fortune, and you’re in too deep to turn back now.

Step 2: One Software, Many Prices

Next, we break the news: you don’t need just one piece of software. You need many. Each tool is sold separately and, naturally, priced per user. But don’t worry, we’ll bundle it for you and call it “seamless integration.”

Don’t forget, you’ll pay per head for every single employee, even if they’ve never logged in or clicked a button. That intern in accounting? Yep, they cost you. The janitor? If they’re in the directory, they count too.

And don’t even think about scaling. If you hire 10 new people, the price goes up. Fire 10 people? The price still remains because somewhere in the fine print, there’s a clause about minimum adjustable headcount fees. It was sold as a discount to your advantage…

Step 3: Want a Feature? Talk to Sales

You’d think enabling a feature would be as simple as toggling a switch as in “seamless integration”. Not in enterprise software!

If you want a feature turned on, you’ll need to book a meeting with one of the salespeople. They’ll smile, nod, and show you how the feature will revolutionize your business. Then they’ll hand you a quote that makes your CFO faint.

Of course, you’ll pay per head for the privilege of using this feature, which was probably built in six months by an overworked developer team. But don’t worry, our sales rep just earned a fat commission, so at least someone is happy.

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The absurdity of enterprise software pricing and rigidity became painfully clear to me. When I saw an entire stack of workflows and applications, costing over $15,000 a month, silently replicated by a single employee, I gasped. How did he do it? By signing up for a service that costs just $100 a month.

This wasn’t a one-off, either. It was a stark reminder of how bloated and unnecessary many enterprise tools are. That $15k stack wasn’t just overkill, it was actively stifling innovation. And yet, when the $100 service was revealed, it was dismissed as "not enterprise-grade," even though it did the job perfectly well.

In another company, we collectively hated our Oracle database. It was expensive, clunky, and an all-around headache. So, a small group of us decided to quietly build a replica using MySQL. The result? A more flexible solution tailored to our needs, and it didn’t cost us a fortune.

Unfortunately, our little project caught wind somewhere in the upper echelons of management. That’s when we learned we had a 10-year contract with Oracle that legally bound us to use their database for our services. It didn’t matter that MySQL was better. It didn’t matter that it saved time and money. We were forced to scrap the entire project because, in enterprise software, contracts trump common sense.

More Enterprise Shenanigans

Let me share another story that sums this up perfectly. I once contracted for a company that built websites for large nonprofits. These weren’t groundbreaking, AI-powered platforms. They were WordPress sites with a press release section. Simple stuff.

They charged $35,000 per website, with a standard delivery time of six weeks. Here’s how they justified the cost:

Every single person in the room was part of the project. The manager listed them one by one, the designers, the copywriters, the consultants, the salespeople, and finally, the two developers (including me). Each person was deemed “indispensable,” and their time was meticulously calculated using Glassdoor salary data.

By the end, it all added up to $35,000. Was it fair? Sure, if you think of it as paying everyone’s salary for six weeks. But the website itself? It was nothing special. You weren’t paying for the product; you were paying for the elaborate machine behind it.

Here’s the thing: enterprise software doesn’t suck because it’s inherently bad. It sucks because it’s designed for the company selling it, not the one using it.

It’s not like “Oh, this sucks; I could build something better in a weekend.” No, it’s more like, “This is clunky, inefficient, and overpriced, but they charge me whatever they think I’ll tolerate because I have no other choice.”

So, why do companies put up with this nonsense? Because it’s a racket, and once you’re in, you’re stuck. Enterprise software is the ultimate trap. Designed not to solve your problems, but to create just enough new ones to keep you paying forever.

If you’re wondering why it feels like you’re paying a Ferrari price for a 1997 Honda Civic with a sticky gearshift, welcome to the club. It’s not just software; it’s enterprise software. And in this world, mediocrity costs extra.

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