Hi Divyansh,
check out my earlier response here. but to add - in our case we were able to build a singular platform that supports the needs of small and large organizations (and obviously we keep advancing the product experience). We have self-service, light-touch, and heavy sales touch based on what buying experience is right for the customer and similarly, we have low touch self-service customers success resources as well as an enterprise customer success team to help our large customers.
We started bottoms up, then layerd on top a light-touch sales motion and then layered on top a heavier touch sales motion, similar with CS. It was a deliberate process and we let the market pull us up. (but we know we would go upmarket and were intentionally building the foundation for it).