Fox News Five spent some time debating this one last night. "Of course Obama knew." "Sibelius certainly knew." "Somebody knew, why didn't they tell him?"
From the sounds of it, nobody on the Five has the slightest idea how software projects work. Only the techies, programmers and engineers actually on the project have any idea of how things are going. And, in some cases, nobody on the job has the slightest idea what's going on. On a big job, you have to divvy up the coding to a large number of programmers. All of whom settle down at their keyboards and furiously punch in code. Ask one of these guys how he is doing and he will say "Great". You don't really know anything until you put some (or all) of these guy's code together and test the whole system. This doesn't happen until pretty late in the job. And, unless there is a good project engineer who insists on serious testing, it won't happen. Nobody likes testing, it's hard, it's dull, and it shows up flaws in YOUR code, and nobody likes that. If the project engineer doesn't push testing, it doesn't happen. In that case, the customer serves as beta tester, and nobody knows how broke the system is until they release it.
There was no prime contractor in charge of the whole Obamacare project. They divvied up the work inside HHS and let contracts to companies them selves. I seriously doubt that any GS type at HHS knows squat about software projects. If there was a project engineer, he has laid really low since SHTF. It's most likely that nobody at HHS had a clue as to where the project really was.
And the suits anywhere have a problem knowing what's happening. Only the best of project engineers has much of a handle on his project. If a suit tries the "management by wandering around" bit, and talks to the guys on the project, he will find a couple of doom sayers, a couple of polyanna's, a bunch of "duhs" and he won't be able to identify the few techies on the job who actually know what's happening. You have to be a techie yourself to tell one from the other.
It is entirely plausible that nobody at HHS knew what was going down. In that case, Obama wouldn't have known much either.