Earlier quoted context omitted.
They coasted on momentum for half a year. I don't even think it says anything negative about the current CTO, but more of what an exception JGC is relative to what is normal. A CTO leaving would never show up the next day in the stats, the position is strategic after all. But you'd expect to see the effect after a while, 6 months is longer than I would have expected, but short enough that cause and effect are undenia…
You can coast for quite some time (5-10 years?) if you really lean into it (95% of the knowledge of maintaining and scaling the stack is there in the minds of hundreds of developers). Seems like Matthew Prince didn't choose that route.
This is the key individual paradox: they can be a massive asset and make the impossible happen but if and when they leave you've got a real problem unless you can find another individual that is just as capable. Now, I do trust JGC to have created an organization that is as mature as it could be, but at the same time it is next to impossible to quantify your own effect on the whole because you lack objectivity and your underlings may not always tell you the cold hard truth for reasons all their own.
And in this case the problem is even larger: the experience collected by the previous guru does not transfer cleanly to the new one, simply because the new one lacks the experience of seeing the company go from being a tiny player to being a behemoth, and that's something you can do only once.
I've always been of the opinion that without JGC Cloudflare did not stand a chance, irrespective of those hundreds of developers. And that's before we get into things like goodwill.
And of those hundreds of developers you have to wonder how many see the writing on the wall and are thinking of jumping ship. The best ones always leave first.
I would not be surprised at all if this whole saga ends with Google, Microsoft or Amazon absorbing CF at a fraction of its current value.