The root problem here seems to be that the CTO had no clue how long that feature would take to build; that seems like a criminal blunder for a Chief Technology

The root problem here seems to be that the CTO had no clue how long that feature would take to build; that seems like a criminal blunder for a Chief Technology Officer, who can’t estimate technology work! This seems like the pattern in general though - successful tech companies (though most “tech” companies today are not really that) only succeed if the person at the helm has the ability to tell tech from bullshit. Or you need to have a truly trustable confidant who you can fully trust on their opinions (which honestly is rare looks like). Without that ability you’re left to either guessing or depending on judgements of people beneath you who almost never have a fully aligned incentive to be honest either deliberately or just instinctively. If anything their incentives are often anticorrelated. I also think this is the issue with most pharma biotechs. gSK is (was?) run by a lipstick maker. What do you think their ability will be to tell if an IND is gonna actually work? You end up having to trust the CSO who might have more interest in making sure their drug gets to market than their eventual success.