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Possibly due to this person having exceptional stakeholder management skills.

Speaking as someone who works in management. Knowing the difference between key stakeholders that you cannot afford to lose, and ones that are disposable are essential.

This is the million dollar question. I think there are cases where executives take this kind of aggression like it's tough love and so they argue with the warlike technical folks but ultimately concur, like old habits dying hard

There were factions and he was in one that had his back. The faction that belonged to a new CEO who brought with him a CTO. Most of the antics and cringy back stabbing flowed from the CFO who was brought in by other board members.

After we got acquired he started openly insulting management and the new company to their face in meetings in front of everyone. He did it on purpose but it still took quite a bit to get fired.

> Was it life or death for the startup to achieve "world class compliance"?

Most likely.

Nobody cares about security until they lose actual money because of it.

After that, your CISO now has the budget and importance defined by how much money the company got taken for.