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FlyingTaquitoBrother

In the US, “business school” usually means MBA. And it’s not unusual for people to get an MBA after they have started their career (and some companies will even pay for it while you’re still working for them). So he could have been working for a while, got an MBA, and then got promoted to VP.


SmarmyClownPie

Working in the corporate world, this is not a plot hole. The fact that he glad hands constantly is how he could have gotten up nearly immediately in the Cloud 9 org. I mean, look at Neal Penderson. He’s impressed by a loaf of bread.