I think it's one of the biggest growing pains a startup has going from a couple people to double digits. My particular comments are from Cincinnati's startup e

I think it's one of the biggest growing pains a startup has going from a couple people to double digits. My particular comments are from Cincinnati's startup ecosystem, where I've been an engineer for a few startups and hang out with founders around our local accelerators and incubator regularly. I think Chicago's is comparable in some ways -- the biggest differences being you have a more mature ecosystem and more funding, and some huge startups which we definitely don't have. I've seen management-level people come in without background experience that handle the managerial parts of their job well. I've seen some people get promoted from head of whatever to their first management position and become not good at both. However, managers with prior management experience at a startup seem to be the best bet. Sometimes skilled management that has a background outside of startups does well; sometimes I think they hurt the early- to mid-stage culture. I've also seen, at the early stage, CEOs that have never done project management or managed developers before and they are bad at one or the other. Honestly, I think this just varies widely by company. It's never been something that's affected my choice to (not) work for / stay with a company though. Personally, if traction is good and you enjoy the team, I tend to just have confidence the founders and management will figure it out while I mostly stay heads down on engineering. Perhaps that's a little vague and not the most helpful answer, but it's a reflection on my startup experience.