At my last company, sales was the thing that broke me. I cried every day trying to learn it. Rejection after rejection—it was a gut-wrenching, vulnerable, and downright terrifying place to be as a technical founder.
Fast forward to today: I’m building Empromptu, a new company in the post-AI era. And I’m making myself do it all again. But this time, with AI.
Can AI help a technical founder not just survive sales—but actually get better at it?
Let’s find out.
I ran every sales call through an AI note-taker. Transcripts, action items, moments of panic, awkward silences—all captured without me lifting a finger.
I had a bad demo. Like… "please let the Zoom connection drop" bad.
Instead of hiding from it, I dropped the transcript into GPT and used this prompt:
"You are an expert Chief Revenue Officer. Your sales rep just had a bad demo. Using the best sales techniques, create a better, more convincing demo of the provided transcript. Go step-by-step through the customer’s needs and everything you know about Empromptu. Don’t hold back. Don’t sugar coat. Be clear and direct. Guide them on what was confusing, how to handle objections, and what they should say instead."
The feedback was brutally accurate—and exactly what I needed.
No more blank pages. I used GPT to test 3–4 different angles for how to explain Empromptu’s value to different personas (compliance teams, data science leads, product teams). Then I ran each one through Empromptu to get a quality and tone score.
Let’s be clear: you can use AI to help you scale, test copy, prep demos, and track learnings. But no tool—not even Empromptu—is a substitute for the founder doing early sales themselves.
You need to be in the trenches, hearing objections, watching body language, iterating in real time.
Early sales strategy is founder work. You can’t outsource product-market fit.
But AI? It makes you sharper. It shows your blind spots. It gives you coaching feedback at 2am. And it makes the whole painful process just a little bit faster.
AI didn’t turn me into a world-class seller. But it did:
And when paired with Empromptu, it helped me turn vague "AI stuff" into sharp, repeatable messaging that actually lands.
If you’re a founder doing sales for the first (or second) time, I feel you.
Next up: Using AI to build an outbound engine from scratch.
Follow along here or at empromptu.ai/blog.
