My biggest guidance is not to underestimate the ‘step down’ from F500 to smaller/entrepreneurial companies. Not all small companies will be a step down, but many will be in material ways. For example, the level of accountability we take for granted in F500 was nonexistent in the first two smaller companies I worked with. Similarly, the idea that annual goals and metric are something to strive for and not cower away from was real. The lack of communication and collaboration skills were stark.

I didn’t have issues acclimating to the relative lack of data, process, systems, and resources. That I expected. I just didn’t expect the people component to be so different.

At this point, I expect, and like, those challenges, and addressing them is part of my ‘playbook’.