Either my mom, my uncle, or my grandma, taught me the most important lesson in sales.
Go straight to the top.
This seems to work well for a number of reasons.
Number 1: Less people are trying to sell to top level managers, so they are a little more inclined to listen. Note that I said a little.
Number 2: They are the decision makers. Once you get a yes, it trickles down. Get a yes at middle management, and you still have to convince those guys in the penthouse.
Number 3: Upper managers are often more chill. Middle managers are still trying to fight their way up the ladder and are focused on their career growth, whereas upper management is a little more focused on the company success. Again, I said a little.