Flexport CEO resigns a year after joining logistics company

I heard him talk at a conference once and thought his insights were somewhat benign for someone in his position, but he didn't strike me as evil. Just uninteresting, I guess.

It's as if the efficacy of a business isn't completely positively correlated with the coolness of its tech stack. I work for one of their competitors, and I'd kill for their tech stack. But ultimately their business revolves around a bunch of professional logisticians and customs brokers being able to execute reliably and effectively, and all tech can do is enable this. I wonder if they realize this.

I have often thought about this throughout my career, both being in the reporting chain of said star, and once being that star. The fundamental thing is that a persons performance in a role is much less under their own control than even they often expect. So why is that? Especially in management roles?

People have a reputation that permeates the organization they lead. It will have plusses and minuses, fans and haters, but generally there is a tremendous amount of context about how they lead and how to interpret their actions. There is also a tremendous amount of history about their choices and how they have dealt with both good and bad outcomes from their choices.

Additionally, people who have been in an organization a "long time" (years) and especially if they have "grown up" through that organization, have a really solid network of other folks they can turn to who both know what they can do, and understand what they are asking.

When you change jobs there is a "honeymoon" period where what you do, or don't do, can always be ascribed to "they are new here." It is imperative that new leaders use this period to "course correct" to get to a point where they can effectively lead the new organization they are leading. This is the most important thing they need to do in their first 100 days. Even if you are dropped into a complete dumpster fire, understanding how to "wield" your organization is critical if you want to actually address the fires. On at least one occasion I watched a VP Eng parachute into an org and flame out horribly (even though they had the chops to get the job done) because they focused on "getting things back on track" before "getting to know the organization."

If you work for someone who is new and "previously experienced" (which is to say they got their experience somewhere else). Helping them learn the ins and outs of the organization will benefit both you and them. You because you won't be subjected to obviously stupid decisions which are only obvious if you know how the organization works, and the "new guy" (assuming they aren't a sociopath) will appreciate your efforts and look favorably on your future inputs.