645 - The CEO Behind The Deal

The CEO Behind the Deal: Why Buyers Look You Up Before They Say Yes

Before a deal closes, someone on the other side has already looked you up.

This is not new. It happened before AI, before LinkedIn, before search engines made it frictionless. What is new is how thorough that process has become, and how little room there is for a CEO to be invisible or vague.

Working inside a large organization, I was involved in procurement conversations at a global scale. The process had a structure. Vendors were evaluated, validated, and compared. That part was handled by the team. But when a conversation moved toward something significant, something strategic, what I did was look up the person. Not the company. The person.

If the decision involved a global program, I would find the CEO. I would read what they had written, watch what they had said publicly, try to understand how they thought about their business and their people. The question I was trying to answer was not whether their company was qualified. That had already been established. The question was whether this person's thinking aligned with where we were headed.

That is a different evaluation entirely.

At scale, the formal procurement process filters for capability. The informal process filters for fit. And fit is assessed through what is visible about the person in a leadership position. If nothing is visible, the assessment still happens. It just fills in with assumptions, with silence, with whatever fragments exist.

This pattern has not changed. What has changed is the tool used to conduct it.

A buyer today can open a conversation with an AI system and ask questions about a CEO that would have taken hours of research a few years ago. The AI synthesizes what exists publicly. Articles, interviews, podcast appearances, and published points of view. If the record is thin, inconsistent, or absent, the synthesis reflects that. The buyer forms an impression before the meeting begins.

The CEO who has not considered this is operating as though the buying process starts when the conversation starts. It does not. Over time, the research happens earlier and earlier, and the impression formed before the room is harder to shift inside it.

The issue is not whether a CEO needs to be findable. Most already understand that visibility matters. The issue is that findability is now a system. It requires consistency, a documented public record, and the kind of clarity that holds up when run through an AI query at two in the morning by someone preparing for a conversation you do not know is coming.

Reverse engineering that system starts with understanding what the person on the other side is actually looking for. Not credentials. Not a company overview. A sense of how this leader thinks, what they stand for, and whether that is coherent over time.

That coherence is what gets built slowly and read quickly.

Highlights:

00:00 Brand vs Personality

00:25 IKEA Procurement Example

00:40 Researching the Decision Makers

01:01 Being Findable in AI

01:31 Reverse Engineering Visibility

Links:

https://www.jensheitland.com/links