Ten person startups (or smaller) often have a lot of generalists. Everyone does a little of everything, which is what can make startups exciting. When you grow past 10 people to 15 or 20, that structure starts to break down. All of a sudden the generalists in slash positions will move from two part-time jobs to two full-time jobs and will stop being effective. The people who depend on generalists will stop being effective too. A few years ago, we scaled from 10 to 20 people. In hindsight, there are some things we did well and other things I would have done differently. Here are my lessons.
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