Biggest pitch to date. $2.3M enterprise deal.
I’d rehearsed for weeks, knew every slide by heart.
This was their masterclass on ”how to sell to Fortune 100.”
15 minutes in, I’m walking through our endpoints when the CEO cuts me off:
“This is a waste of my time. You clearly don’t understand our business. Justin, can you take over from here?”
Then, looking directly into the camera at me: “Amanda, you can drop off now.”
Dead silence.
I could see my team’s faces in the gallery - all frozen.
I mumbled something about “any follow-up questions” and left the call.
Sat staring at my blank screen for 20 minutes.
How do you recover from getting kicked off your own sales call?
That night, I replayed every second. What went wrong?
I realized I’d been selling like a vendor, not a peer. I was demonstrating features while they needed solutions. I was talking about our product while they cared about their problems.
Authority in sales isn’t about knowing your product better than anyone else. It’s about understanding their business better than they do.
Next Fortune 500 call, I flipped the entire approach. Spent 45 minutes asking about their operational challenges before sharing my screen.
“Walk me through your biggest bottleneck.”
“What keeps your team up at night?”
“Where are you losing the most money?”
By the time I opened our demo, I wasn’t showing features - I was solving their specific problems in real-time.
I lost that original $2.3M deal.
But that humiliating 15 minutes taught me how to sell to enterprise.
Now we close customers like HubSpot, Klarna, and Datadog.
Sometimes getting kicked off the call is exactly the wake-up call you need.
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