started talking to people inside the company, one conversation leading to another, until he had sat through roughly 30 meetings across the organization. Somewhere during those conver-
sations, the nature of the sales call changed. He was no longer trying to sell something. He was trying to un- derstand something. Eventually he found it: a problem serious enough to threaten the CIO’s job. Now he had a reason to go back, and this time he wasn’t carrying information about his product. He was carrying insight about the CIO’s own busi- ness. From that point, it took six weeks to close a $4.2M deal. When John, the creator of The Compass – the Sales Strategy Operating System designed to help companies make their number – told me the story recently, I realized that the CIO had unintentionally written the job description for every salesperson working today. “Come back when you can tell me some- thing I don’t know” is no longer one gruff executive’s dismissal; it’s what every customer can now say to every salesperson, because AI has made it possible for them to know almost everything in advance.
THE END OF THE INFORMA- TION ADVANTAGE For most of the history of profes- sional selling, the salesperson held an information advantage. We knew the products, the competitors, the implementation risks, what other customers had done in similar situa- tions. The salesperson’s knowledge created value on its own. However, the Internet chipped away at that advantage – and AI may finish the job. A buyer can now sit down before your meeting, ask a model to compare your product against three competitors, surface the weakness- es, generate hard questions, and summarize the entire category – all in a few minutes. So I asked John the question that follows naturally from his own story:
If information no longer gives the salesperson power, what does? His answer was the same thing that got him back into the CIO’s office three decades ago. Insight. And he was precise about what he meant, because the word gets used loosely. Insight is not a fact the customer happens to lack. It is something about their business – and about what your offering would do inside it – that they have not seen for themselves. Notice that the buyer’s own AI cannot produce that. The machine knows their industry and it can read your Web site, but it does not know what your capability does once it is running in their operation, and it has never sat in the room. That intersection is the salesper- son’s ground, and it may be the last ground that is genuinely theirs. Getting there takes judgment, because of something strange that happens as AI gets more capable. It can hand you five paragraphs of confident, well-written analysis, two of them exactly right and three of them completely wrong, and all five will sound equally intelligent. The salesperson’s new job is to know enough to catch the machine when it is wrong, which means the value has shifted from possessing infor- mation to knowing what the infor- mation actually means. And there is a simple economics underneath this. AI will generate all the tactical options you want – 10 ways into an account in seconds – and most of them will be perfectly serviceable. Producing options has become nearly free. Knowing which one is right has not. That is precisely what John did
on Wall Street, before any of this technology existed. He gathered fragments that already sat scattered inside the CIO’s organization and assembled them into a picture no- body else had seen. AI can now help collect those fragments at a speed no human ever could. It still takes a human being to decide which frag- ments matter.
‘‘
The true sign of intelligence is not knowledge but imagination. ALBERT EINSTEIN
FROM TACTICS TO STRATEGY John reached for a second story to make the same point land differ- ently, and it stuck with me because it reframed everything we had already discussed.
A major league pitcher commands four or five pitches. Which one he throws depends on who is at the plate, the count, who is on base, what inning it is, what this hitter did the last three times up, and doz- ens of other variables. He has only seconds to weigh them all. That is strategy. How he throws it, the grip, the mechanics, what his body will let him do, that is tactics.
Most salespeople, John told me, have one pitch: a fastball. And most sales organizations spend their training budget teaching people to throw it harder – drilling the script, the methodology, the deck, the discovery questions, and the objection handling – rather than asking whether a different pitch was available. That is exactly the kind of tactical execution AI is becoming extraordinarily good at helping us do. Which means the human value in selling is migrating to strategy. To the person standing on the mound deciding what to throw – the same shift from information to judgment we had already been circling. What struck me is that John does
not treat this as a gift. He treats it as a discipline. A pitcher learns to read a count. A seller can learn to read a deal, and the reading can be taught, structured, and repeated. That is the bet behind The Compass. When there is uncertainty, develop strat- egy. When there is certainty, execute
SELLING POWER SEPTEMBER/OCTOBER 2026 | 13 © 2026 SELLING POWER
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