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 $$$ for a dead-simple form + button if it eliminates a workflow problem. They really could care less if it looks like it's from the 90s (most of their stuff looks that way, anyway).
I agree with your point - If a product solves a real problem, design/usability is a secondary concern. This is particularly dependent on the space, in my experience. In my fintech world, a bank will give you a massive amount of $$$ 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).