When you work with large enterprises, it is tempting to think you are selling to an organisation.
A logo. A department. A buying committee.
You are not.
You are selling to a person with a personal agenda that usually comes before the company agenda, even if nobody says that part out loud.
I learned this the hard way.
We had built a comparison module that stacked our solution against competitors.
Clean. Honest. No gimmicks. We genuinely won most of those comparisons.
I leaned into it hard.
Emails. Copy. Campaigns…
The tone was confident, almost aggressive.
We are better.
Others do not work.
This is why you should switch.
One day our CEO pulled me aside.
Not angry. Calm. Experienced.
He said something that completely reframed how I think about enterprise selling.
People have agendas higher than their company’s agenda.
If you openly trash a solution, you might be trashing the decision they personally defended last year. The tool they convinced the board to buy. The vendor they built political capital around. In that moment, you are not positioning your product. You are undermining them!
And buyers protect themselves before they protect roadmaps!
That was the blind spot. We were talking to companies. Our message was landing on people.
Enterprise customers are not neutral evaluators. They are operators navigating risk, reputation, and internal politics.
If your message makes them look wrong, careless, or outdated in front of peers, they will quietly disengage, even if your product is better.
The shift was subtle but powerful.
Since then I’ve moved from replacement language to gap language.
Not your current solution is broken, but here is what it does not cover.
Not why others fail, but where teams usually struggle as environments evolve.
The product did not change. The posture did.
Something else changed too.
Our buyers started sounding smarter in internal conversations.
They could explain why an addition made sense without admitting a mistake.
They could frame the decision as progress, not correction. We were no longer threatening their past decisions.
We were strengthening their current position.
That is the difference between winning an argument and winning a deal.
Enterprise sales is not about proving you are right.
It is about helping someone be right again, in front of the people that matter to them.
Your customers are not companies as organisms. They are people in seats.
Make them look good.
Everything else follows.
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