How to Win Deals in the Age of AI | Alex Lieberman
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How to Win Deals in the Age of AI
Alex Lieberman August 20, 2025 · 2 min read
IN THIS ARTICLE
01 From Pitch to Rejection 02 Engineer Flips the Script 03 Prove Value Fast 04 Conclusion
Here’s a pretty crazy sales story.
Last week, a huge fitness influencer reached out to our team to help develop a mobile app they’re looking to launch. The team was pumped about it. Massive name, great idea, and a clear way for Artificial Intelligence to scale a one-on-one experience.
The pitch went well. The influencer said it was between us and another product and engineering partner, and that they’d get back to us soon.
From Pitch to Rejection
Twenty-four hours passed, and we got a text: “We’re going with the other guys.”
Well, that sucks.
If this was five years ago, things would have gone one of two ways. We’d either pester the lead to get them back on the call to gather information and see if the door was actually closed, or we’d call it closed-lost and move on with our lives. But in an age of AI, things—especially sales—look completely different.
Engineer Flips the Script
One of our engineers at Tenex heard that we lost the deal and took it upon himself to win them back.
Within 12 hours of getting the bad news, he built and deployed a functioning app that could be downloaded and used in TestFlight. He also recorded a Loom video walking the influencer through the app and explaining where we could build upon the Minimum Viable Product if we worked together.
Twelve hours after that, I got another text from the influencer: “Watching this now. Impressed.”
Prove Value Fast
He proceeded to tell us that the door isn’t closed and that he wants to get on another call to see how we can make it work. We had the call yesterday, and while nothing is signed yet, things are looking very good.
It was an absolutely savage move by our engineer, and a pretty cool example of speed-to-value in a post-AI world.
Conclusion
This story is a reminder that sales in the age of AI isn’t just about pitching—it’s about proving.
Key Takeaways:
Rejection isn’t final. A “no” can be the opening to show value in unexpected ways.
Show, don’t tell. A working prototype beats a pitch deck every time.
Speed matters. Delivering value in hours instead of weeks can flip the outcome.
Empower your team. Breakthroughs don’t always come from sales—they can come from anywhere.
Follow me on LinkedIn for more content like this.
WRITTEN BY
Alex Lieberman
Founder & Podcast Host
Alex Lieberman is the co-founder of Morning Brew, the business media company he led as CEO from 2016 to 2021 and grew to more than 4 million subscribers before its $75 million sale to Insider in 2020. He is now Managing Partner of Tenex, an AI engineering and transformation firm, and co-founder of storyarb and GrowthPair. He hosts The Founder's Journal podcast and was named to the Forbes 30 Under 30 Media list in 2018. He holds a BBA from the University of Michigan's Stephen M. Ross School of Business.
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