There's a stage in a startup's growth when that different set of experience is valuable, and at other stages it's often harmful.

I.e. the experience of a manager coming from a 500 person organization is valuable when the startup is scaling to 100 people and is building the structures and processes required for those 100 (and later on 200 and more) to work efficiently; there's a lot of organizational know-how and perspective that would be useful to take into account. The same experience/perspective from the same person are not that valuable and potentially wrong/misleading if you're currently scaling from 10 people to 20.