I'm not sure if lumping Zappos (1500 employees) with GitHub (100 employees) makes much sense. I don't believe the organizational structure has an impact until you get over a few hundred employees.
It's kind of like sports. If you are playing in a niche sport that only has 3 teams then you don't really need committees to maintain the rulebook, a referee union, a centralized body to represent the teams or a players' union.
When you're small enough everything just either works or doesn't. The owners of the company are personally involved, you feel responsible for the success and there's a great deal of transparency.
With that said I do believe most smaller companies should be flatter, and that it starts at the top, like not having a CTO, CIO, VP Technology, Director Technology, Director of IS for a 20 person company.
I don't believe the organizational structure has an impact until you get over a few hundred employees.
Disagree. There are 50-person companies with all the negatives of MegaCorps (bureaucracy, closed allocation). That stuff starts to matter around 15-20 people.
Even before you have actual bureaucracy, if the founders haven't set forth some strong statements on what they want the company to be, there will be political behavior very early on as people anticipate what might come about with growth. Titles are meaningless at 10 people, but people will still fight for them, knowing that (if the organization moves along the default "main sequence") they will be massively important in the future.
I can definitely attest to 50 person bureaucratic companies, having worked in several. I think this comes down to (as Guy Kawasaki puts it) a Bozo Explosion. Hire bad people, those people hire bad people and the politics get bad quickly.
It's kind of like sports. If you are playing in a niche sport that only has 3 teams then you don't really need committees to maintain the rulebook, a referee union, a centralized body to represent the teams or a players' union.
When you're small enough everything just either works or doesn't. The owners of the company are personally involved, you feel responsible for the success and there's a great deal of transparency.
With that said I do believe most smaller companies should be flatter, and that it starts at the top, like not having a CTO, CIO, VP Technology, Director Technology, Director of IS for a 20 person company.