Yes, you should do this as much as possible but… At every startup I’ve founded or been early at, the first 10 weren’t the top 10. Sure a couple of them were, but we also had some utility players — we had a couple junior developers, an early data scientist, etc. Some wanted leadership and weren’t ready, others didn’t want it but were perfect for it. If it all lines up for you correctly then absolutely do what seems natural. But chances are it won’t, especially as you creep towards 50. Expectations are different at every level, hell, even within every person. It’s hard to manage each individual’s expectations as the company grows.