What changes when the person deciding sits at the top of the company.
A team I worked with went in to see a chief executive on a deal worth £300 million. The chief executive shook the lead's hand, looked him in the eye and said he would write the cheque there and then if the team could tell him with certainty they would deliver. The lead laughed, in the very British way you laugh when you assume somebody is joking.
He was not joking. The deal did not close.
Nothing about that failure was technical. The product was good, the price was fine and the references were real. What went wrong is that a team who could have answered the question had never worked out how to say what they were for.
At that level you are not being compared against a competitor's feature list. You are being weighed against doing nothing, and doing nothing is free, needs no business case and has never got anybody fired.
Your job in that meeting is to understand the problem well enough to hold a genuine opinion about it. Companies default to what we do and how we do it when the person in front of them wants to know what changes and what it is worth.
That shift sounds small and changes everything about how you prepare. It means the research happens before the meeting rather than during it, and it means the person you send is whoever knows most about the problem regardless of their job title.
Pitching features to somebody who is buying a decision.
Sending a salesperson where the buyer expected an expert. Senior buyers forgive a lot, including price, and do not forgive the sense that they understand their own problem better than the person in front of them.
Filling silence with noise. A chief executive who goes quiet is thinking, and talking over that is how you lose the thread.
Leaving the cost of standing still unstated, which hands the decision to inertia by default.
Know the buyer's market well enough to say something about it they have not heard.
Lead with what has changed rather than what you have built, because a change is something they have to hold a position on.
Arm whoever is championing you internally with something they can repeat from memory, since most of the buying committee will only ever hear your story secondhand.
Be able to answer the blunt commercial question without reaching for a deck.
Warm introduction beats cold outreach at this level by a distance, and being useful in public is what generates the introductions.
Shorter than you want. Prepare for twenty minutes and be pleased if you get more.
Whoever knows the most about their problem.