I worked for years on the modernization of a critical banking infrastructure system. The problems are manifold. The biggest problem is overall architectural impedance mismatch - switching from a batch system (most of those old COBOL mainframe apps are batch systems) to a service-oriented architecture. This makes incremental replacement extremely difficult. But a cutover? On a system that moves more money in a day tha…
I'll challenge your view that folks in the startup world don't know enterprise. Maybe some visible fraction are the young and inexperienced hipsters as portrayed on HBO, sure, but most of those I know in CTO+ roles actually have a lot of enterprise under the belt. In my case in a B2B play it's practically mandatory, in order to understand the customer.
I believe enterprises suffer principally from the fear of change, or more bluntly, the fear of screwing up and being held accountable, which leads to the pathological technical debt issues you've described. So the problems I've always faced in enterprise projects are not primarily technological, but instead those of a) finding a full team of people competent enough and fearless enough to perform transplant surgery on the beating heart of a living body corporate and b) collecting sufficient clout to be allowed to perform the operation.
I reckon the best thing you can do, as a project leader in the enterprise world, is leave a legacy of constant and gradual change. Normalize frequent updates through CI/CD. Get business owners used to things like minor feature requests being included in daily deploys. No-one will thank you at the time, but a change in culture is almost certainly the most enduring value you can create.
So yeah, I'll happily roll my eyes at the "incompetence of the enterprise world", because I've dealt with the stupid head-on, and used techniques from startup land to innoculate it permanently.