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Did the CEO/CFO not see this one coming? Or was it a calculated gamble they took and lost on?

They were enjoying the years of free* VC money before the recent interest hikes were made.

And the time to IPO was in 2019 when everyone there was heading for the exit as I said before. [0]

At the time, Stripe said they can wait, no time to rush for an IPO. Now they know they need to IPO before their employee options expire and the down-rounds coming in.

[0] https://news.ycombinator.com/item?id=20993919

CFO departed mysteriously very recently, so maybe there was something there: https://www.axios.com/2023/02/03/stripe-cfo-suryadevara-step...

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