It's often underrated how much an otherwise competent team can crumble under technical debt (of which CI and test flakiness is one specimen).
It sounds plausible to me that slack's rapid growth curve put them in the perfect position to accrue massive amounts of debt from which they are struggling to wade their way through.
Yes. But also requires management who can understand and value what they have in that team.
Before you have it, you should be willing to accumulate large amounts of tech debt both because your product might change enough that you'd be rapidly throwing out large amounts of code anyways and because having product-market fit is such an overwhelming need that almost everything should be traded against it because your startup is dead without it.
After you have it, you have to be much more diligent about paying down tech debt, because you switch from a more "exploratory" mode to a "refinement" mode where you now are unlikely to be throwing away large swaths of your code at the drop of a hat, and instead need to iteratively build upon what you already have and that becomes very difficult to do with large amounts of tech debt.
I honestly think that the glacial pace of software engineering is mostly due to this phenomenon -- "where can we save a little bit of time today?" and then it snowballs into entire teams not getting anything done. The interest on the loan they took out is higher than their income. I guess that's why they call it technical debt. (Does that make Scrum Masters technical loan sharks?)
Developers who don't get that intuitively quickly learn it when they get the wrong type of questions after the wrong type of updates.
Tail wagging the dog.
Their support is great and responsive though (I've reported every issues I've encountered)