Couldn't agree more. In my experience leading sales teams the difference between one territory rep versus another territory rep is how well that rep was trained/motivated/coached and mentored by his sales manager. Stellar VP of sales are not only good with customers but also exceptional at grooming people. Aiming high and poaching from a Facebook, Google etc. is the right thing to do as these companies have good sales folks. If you are looking at enterprise sales then Oracle and Salesforce.com have stellar people. But I imagine some kind of inflection point in the startup journey where it makes more sense to hire a VP of sales versus a individual contributor sales rep. Any pointers on what that inflection point would be? Funding?

I think inflection point would be determined by: a. Funding - I mean, you need to pay these guys a bunch. Equity can get you only so far b. Stage - I think hiring a stellar VP of Sales with a half-made product is not going to play out well.

any other ideas?

Also, does the startup have a semblance of a repeatable business model (which tends to be correlated with later rounds of funding)?

If you know by putting in X sales reps with $Y sales productivity per rep you can achieve $Z (X*$Y) in sales then that is a good case for hiring a VP of sales and have him build a sales organization under him.