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>> I think the real value employees get is riding the rocketship in their career.

Startups hire those people when they are risky and the future is unclear. Once there is traction, the VCs and insiders bring in friends for cush Director/VC posts. Quite often the people who took the real risks get left out.



And that seems like safe capital preserving thing to do. A director role isn’t a prize for loyalty, it’s a job with a skill set. Your second programmer isn’t going to be as good at is as some guy who has been a director 6 years else where


Sorta. A very common pattern is for startups to make abysmal hires for these "executive" roles, because the people in those roles in big tech bring loads of politics and a very narrow type of experience. They bring in their friends, and it isn't terribly long before the people who got the company to the place of initial success are gone. I've seen this play out many times.

Not to say that the early employee is necessarily guaranteed to be better, but at least they're a known quantity, have demonstrated loyalty, and have loads of business context that the shiny exec hire won't have.


Good points about roles not being prizes (unless that was the deal, which it sometimes is), but I'll devil's advocate this anyway.

> Your second programmer isn’t going to be as good at is as some guy who has been a director 6 years else where

If you hire smart people who learn, and who believe in the mission and team... that programmer might well be in the running to lead engineering.

Knowing tech industry a bit, I'd be at least as skeptical of directors from outside. Of course I'd have to consider them, at times. But I expect at least half of the outside candidates for leadership roles will be disingenuous halfwits.

Meanwhile, if you've got people who had the grit to help get you to that point, and demonstrated alignment and loyalty when it mattered, and who foster that trust in your company culture, then you'd be an idiot not to try to find a way to get rare goodness like that in your leadership.


The CTO of Grab (my employer and $10b company) was an early engineer hire. Same for a lot of the L7+ talent.


You’re not wrong, but I don’t think 100% of the high level roles are filled this way.




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