Many enterprise products have bad design because they need to serve so many complex workflows, not because their design teams completely suck. It's just a hard problem (eg look at Salesforce and tell me how you'd design it well...)
Consumer products are like Chipotle: streamlined menu, built for efficiency and elegance. Enterprise products are like the Cheesecake Factory: you want a steak, pasta, pancakes, and a margarita? Go for it! Why is there a full f*ing bar in the back? Who knows!
It's hard to have great design when you have to do so much.
I would say Craigslist because it's not pretty but I can't say that an ugly UI is the same as a horrible design. The design has worked well so far for many types of people.
IMO it feels like AWS just makes slow gradual changes without trying to match the material design updates etc of other clouds - all while knowing the ideal usecase of their platform is automated through the API with tools like terraform.
Most teams look at the data, and see that a vast majority of their customers use the CLI. I'm sure AWS loses out on sales from non-technical folks who only see the console side of things, but I personally would way rather DynamoDB focus on performance rather than a pretty console.
That isn't true for all though, many AWS services seem like they are 'console first' and do wonky shit in the console that is hard to do using APIs. Those services are incredibly frustrating.
Most AWS teams own their own console from what I've read here. And the smaller orgs often don't have any designers - backend engineers build the first iterations of the console.
I just wish the read interfaces were better. They could not even build configuration/creation/update interfaces and I wouldn't even notice. In 2020 who is even manually spinning up resources. But looking at lists of resources and statuses is still something I do consistently.
All the cloud providers reached success with awful UIs (IMO), which was temporarily solved by abstracting away from their UIs with Infra as Code and other tooling. They're getting around to updating it in recent years, though.
I agree with your point - If a product solves a real problem, design/usability is a secondary concern. This is particularly dependent on the space, in my experience. In my fintech world, a bank will give you a massive amount of $$$ for a dead-simple form + button if it eliminates a workflow problem. They really could care less if it looks like it's from the 90s (most of their stuff looks that way, anyway).
What are other software products / companies with horrible design but get the job done?