I previously discussed some things about working in a large organization that I was happy to be rid of. This is the other side of that coin.
These things are by no means exclusive to large companies. They are rather hallmarks of a mature one. But, it has been my experience that this correlates with size. I've worked for a variety of companies and industries, and that trend has held up in my view.
All of this really boils down to institutional experience, or something like that. The earned knowledge of how to enable people to work together smoothly. How to recruit good talent. How to retain the people you hire. How to keep people happy and healthy and satisfied in their careers. Larger and older companies have an advantage here because they have a deep roster to draw from, and because they've had time to make these mistakes before. But, there's no reason that a small company can't have this knowledge. There's no reason that a young company can't have this knowledge. To really get it, they would only have to prioritize getting it. That would mean recruiting experienced people whose job it is to provide this knowledge: HR, management, executives. Taking the founders and just saying that they are filling those roles is not likely to cut it. At a minimum, it would also require those founders to make an honest assessment of their strengths in this area, and then work to fill in the gaps. It's not sexy, but it's how you keep things moving in the long term.
Starting a new project is great. It's everyone's favorite part of the job. And if it's going to be successful you have to really understand the problem you're trying to solve. A mature organization starts by researching the problem, and the market, and the competition. You get some idea of the end goal, and then trim it down to something minimum viable that you can get working quickly and iterate on. But that's a lot of work. That's not moving fast and breaking things. And so an immature organization will just start and figure it out as they go. Of course the problem is that "move fast and break things" was terrible advice in the first place and even Zuckerberg realized years ago that going fast means doing quality work that doesn't have to be constantly re-done.
Health insurance should be the start of a benefit package, not the whole thing. I know that we're all unicorns and we're going to be the next Facebook and become billionaires. Except that we can't all be unicorns, and most people aren't Mark Zuckerberg. And even if we are in that exclusive club, I'm working for salary—not equity. So retirement savings, health savings, training, vacation and other time off; all of that is important. And hey, maybe even some equity.
I know I complained about the org tree in my previous post, but it does have some benefit. There are times when you need to know whether someone is a peer or a superior. In the nebulous world of small start-ups, it's very possible for someone to be both. Or neither. And whether they are or not can change depending on the mood of the founder/owner/"10Xer". That makes it difficult to share honest feedback with your coworkers. And all the more so for sharing feedback with that founder.