This is part of my job, buying from the side of large companies so I will provide some input.
This is talking from the direction of actively engaging a large business and selling to them. I work on the side of large business actively choosing which startups we want to work with.
"Lesson 1: In larger organizations there are multiple individuals with separate motivations involved in the buying process "
Without question this is important. I am sort of a gatekeeper in the process. It's my job to validate the companies that are seen by the real decision makers (not me). I am the technical grunt in front of the process allowing the C level decision makers to only make good decisions no matter what they decide to do.
With me, you can discuss tech on a geek level, and I'm most comfortable and at home.
To my C levels, you better be high level and respectful. We've lost the ability to work with several startups simply because they weren't able to discuss on a C level.
If you are a founder and can't discuss on a C level, hire someone who can. You could lose a tremendous level of money and momentum simply because you have no idea how to talk to someone who leads a large business.
The reality is, I wouldn't be good at it either. I do well with our C levels, but they know I do good work for them, and am an employee. I think that changes the dynamic.
If I were in a startup (I have been) I would have someone else do the talking to C Levels, not me.
And even then, my job isn't to make the startups look good in front of our C levels, it's to pick out software for us to potentially use or buy. It's the VC's job to adequately prepare the startups, not mine.
I've done those sorts of sales talks when I was a tech consultant at Accenture and continue to do some now as a technical founder. I have also heard the pitch from vendors when I was at Accenture wanting me to bring their wares to my clients.
In the end it comes down to being able to communicate and listen well. Be an active listener and find out the problems that the C-level customer has. This could mean the actual business problem (sales needs to grow 10% and it hasnt for 3 years), logistical problems(my teams don't communicate), a political problem (I can't deploy a solution without getting the Network Solutions team invovled) - all are things 1) You should know about and 2) You may be able to fix.
That sounds simple, but it's really very hard to not get too wrapped up in what you and your company are focused on, rather than what this specific customer in front of you right now cares about. The best salespeople of ANY kind are very good at getting in synch with their customers - seeing the world, and their product from their customers POV and then seeing how their product fits into that worldview.
It's a great question, but I don't have the insight on it. My job is on the technical level, and I can just convey to you what happens in a real company.
I don't think I would be the best choice to give the talks. I'd be fine for drinks after.. I'm casually good with C Levels, but I'm a tech at heart, and having me explain things... I tend to do the bad thing of going too technical, and not realizing it before their eyes glaze over.
hmmm it seems like the key is to find the balance between evangelizing your product/vision while genuinely soliciting inputs from the C level on what their priorities are. Hopefully there will be a match somewhere in that conversation