I once lost a massive Best Buy contract because Accenture priced their IT support costs to kill the deal. Their logic: if it works, we get no credit. If it fails, we get all the blame.
That deal died because people I never met with exclusively saw downside risk.
When you sell to the enterprise, it's an iceberg. You get introduced to two or three people. You work hard to understand their needs and motivations. Meanwhile there are a dozen other people, invisible to you, all quietly running the same math: does this get me promoted, or does this get me fired?
Procurement doesn't have to say no. They just have to sow enough doubt. "I don't know if these guys are priced right." "I don't know if the tech is proven." "Maybe we should just wait a quarter." Now your executive sponsor has to spend political capital to overcome these skeptics — and they'll only do that if this deal matters to THEM.
Not to the company. The company will lay them off in a heartbeat if AI can do 60% of their job at 10% the cost.
Them. Their career. Promotion or save job.
I was on a call last week with a founder I've coached for a while. Built a startup selling into the enterprise from day one. They've had a dozen clients over five years. Always two or three active, always slowly bleeding, always six months from shutting it down.
I asked him a basic question. "How many jobs has your product saved? How many people got promoted because they brought you in? How many didn't get fired because of you?"
Half-second beat. "Yeah, probably nobody."
There it is.
You are selling a six- or seven-figure engagement. Somebody's career has to be on the line. Because if doing nothing doesn't hurt them, and doing the deal doesn't help them, they will never go to war with IT for you.
Your champion isn't folding to your competitor. They're folding because of people in the org who whispered "I'm not sure" and went back to lunch.
If you're selling into the enterprise, stop selling to people who nod. Start selling to people who feel like bringing you in improves their career trajectory.
If nobody's LinkedIn profile changes because of your solution, all your deals will keep quietly dying on the vine.