Rule #1 of raising early-stage VC money: never start at the low-end of the totem pole. I actually never realized this when I was running my own VC but I see it very clearly now that I’m on the other side of the table.
Most VCs make their money when they make a contrarian decision. They go against the grain on common and established thinking and when they are proven right, the over/under on that call makes them rich.
Junior folks at VC firms are operating in a very different mindset. For them, the objective is career advancement. So they have a lot more to lose by showing an embarrassing deal to the investment committee, then they would have to gain by taking the risk on a great idea.
So if you are first to market with a great idea that is slightly controversial and un-tested, don’t waste your time with junior folks. Go straight to the top. On the other hand, if you already have tons of big name investors on board, that junior person can be the most aggressive champion for your company. Its all about knowing where you are and which buttons to press.