"Sell High" is a myth. Sell High, Low, and in the Middle

I always laugh when I meet these big ticket "enterprise sales" folks who say they exclusively sell high. "I sell exclusively to the CIO and COO. Because they'll take my calls. Because I'm the man." says the guy in the room with no credibility.

Selling high might get you in the door (and it's a great place to get in the door) but it ain't gonna get you in the endzone. In reality, there are 4 layers you need to be selling to: Budget holders (C to VP level), DecisionMakers (VP to Director), Recommenders (Director to Manager level, usually the folks driving the evaluation), and Users (if there is a pilot or trial process). Key word here is "selling". Not "get in the door". Getting in the door...gets you in the door. The real selling will happen after that.

I can tell you, with 12 years of SaaS selling experience, you need to win all 4 levels. I can tell you that CIOs and COOs are absolutely not getting into the weeds in the evaluation or vetting of software. They aren't. Not in big companies. So stop trying to sell that. They may be the contract signer, they may hold the purse strings, and they may even be reckless enough to overrule their decision makers, influencers, and users based on some political connection, but they are not in the weeds in the hardcore evaluation. That era ended when the first bubble burst in early 2001. (CIOs and COOs putting their reputations on the line to buy software from 30 person startups). Salesforce came along, and COOs (and CIOs) could then refocus on...COO'ing...Don't get me wrong: You absolutely want their support and endorsement of what you are trying to accomplish. 

Ideally you want to win on all 4 levels, but if you win 3 out of 4 you are probably going to win the deal. Go down to 2, lower, 1 way low, and zero...obviously you lost.

The value of selling to the highest tier (C suite) is to protect your flank. You absolutely want their support. But understand that they probably aren't going to throw the game in your favor, because A) They have other people to vet it out B) Why would they put their ass on the line for your startup that nobody has ever heard of? But you have to protect your flank. Your competition may try to wine and dine themselves to a deal. So you sort of have to do that too. But that alone will not win for you. Most of the heavy lifting will be at the next 3 levels.

If wining and dining alone does win the deal for you, then you work at Oracle. Or Salesforce. Or Adobe. Which means: You were gonna win the deal anyways. Because it was probably a (shhhhh) compliance deal. But ring that bell anyways...nice job. And don't let anyone tell you that those are easy calls with procurement. Those can be prickly discussions in their own right.

But in the real (startup) world, you have to play at all the tables.