Stack Overflow's CEO, Prashanth Chandrasekar, wrote a blog post called Accelerating Stack Overflow’s transformation. It's written for investors (more in a bit), but if you read between the lines I think there are some message for the Stack Exchange/Stack Overflow communities too.
Thanks for this post.
Claims of taking the community seriously are still impeded by their utter failure to repair the damage they did and that’s within their power to repair, alas. Just as that blog post is a yarn for investors, I think most of their meta claims are yarns for users. 
But, that aside, I’ve been wondering about their financial situation, too. They’ve taken a lot of VC and I don’t see how they can possibly deliver investor value. But just last year VCs invested $85M for puzzling reasons. What did they see? (What yarns did the company spin for them?)
The company recently replaced their VP of “strategy and transformation”; according to Glassdoor they fired the previous one, along with the CFO and a couple others. Even if the “fired” part isn’t true, that’s a lot of churn at the same time in areas that are directly relevant (especially with all their other churn). From the outside it’s hard to tell the difference between “strategic realignment” and “grasping at straws”.
I hope they tried to do right by the folks on the Talent team; with all their job postings, surely some of those folks could have been transferred rather than fired? I hope?
I gotta assume the idea was something along the lines of:
COVID is accelerating the trend toward remote work and that means companies need to buy more software systems to manage communication. Stack Overflow has a product for that segment, so why not take a chance?
$425M sounds like a lot of money, but it doesn’t seem out of line for recent IPOs. I’d guess that the investors last summer were told they’d get an exit sometime in 2021. It wouldn’t surprise me if the VP and CFO shuffle is something the investors demanded to get people in there who can execute this sort of transaction quickly. As we start to go back to the office (shudder), the story isn’t quite so exciting.
Or maybe the investor last summer just had a ton of cash that needed to be deployed? Investors aren’t always rational. 