That sales strategy is exactly what the sales team at my day job does; our software requires heavy buy-in from IT departments, and the payoff isn't in the IT re

That sales strategy is exactly what the sales team at my day job does; our software requires heavy buy-in from IT departments, and the payoff isn't in the IT realm but more for the foot soldiers on the ground (and of course, the bottom-line). At one point, it became obvious that it was much easier to wine & dine the non-technical executives than it was to win over the CTO. Also, it's a double-win since even if you had managed to win over the CTO, they'd (the CTO + our sales team) would still have to win over the other executives. However, if you flip that around, the CTO is really the only one you have to convince, and if you've made a good enough case upfront then the CTO will have a really hard time stopping it.