I Prepped for 100 Sales Calls Using AI. Here’s What Changed.

Contents

For most of my early career in sales, I prepped for calls the same way everyone does.

I’d open their LinkedIn. Skim their title and tenure. Maybe note a mutual connection. Write one line at the top of my notes: ‘Been at company 3 years. Works in ops.’

Then I’d dial and figure the rest out as I went.

I was decent at it. Good enough to hit quota most months. But my results were all over the place — a great call, three mediocre ones, one that went off the rails, repeat. I couldn’t predict which version of me would show up on any given day.

So I ran an experiment. For 100 consecutive calls, I committed to using AI-powered prep for every single one. Buyer profile first. Roleplay second. Then dial.

Here’s what happened.
 

The Process

Before each call, I opened the prospect’s LinkedIn profile with Dextego running. In about 60 seconds I had:

– Their DISC and OCEAN behavioral profile
– Communication preferences and decision-making style
– Likely objections based on their personality type
– Tailored talking points for someone who thinks the way they do 

Then I’d run a 2–3 minute roleplay through Dextego, practicing my opener and the most likely hard question I’d face  before getting on the call. 

Total prep time: under 5 minutes per call.

What Changed First: Discovery Quality

Within the first 20 calls, I noticed something. My discovery questions were landing differently.

With an analytical buyer (high-C), I’d lead with: ‘I pulled some data on your space before this call — want me to share what I found?’ They’d immediately lean in.

With a relationship-driven buyer (high-I or high-S), I’d open with: ‘Before I get into anything, I just want to understand what’s on your plate right now.’ They’d open up in a way that skipping that step never got me.

I stopped sounding like a rep running a script. I started sounding like someone who’d actually thought about them.

What Changed Next: Objection Handling

Around call 40, I realized I was no longer getting caught off guard by objections.

Not because they disappeared, but because I’d already practiced them. When a high-D buyer said ‘Just send me a one-pager and I’ll get back to you,’ I’d already run that exact scenario in my roleplay. I had a response ready that didn’t sound scripted.

‘Totally — I’ll send that over. Can I ask: is there one thing you’d need to see in it to make it worth 20 minutes next week?’

That came from practice, not inspiration.

What Changed By Call 100: Confidence

The biggest shift wasn’t tactical. It was internal.

I stopped dreading the calls I didn’t feel ready for. Because I was always ready. Not perfectly, but ready enough to show up with a clear game plan and adjust in real time.

My quota attainment went from ‘most months’ to consistent. My deal velocity sped up. But more than the numbers, I stopped leaving calls with that hollow feeling of I should have said something different.

What I’d Tell My Past Self

Prep isn’t about reading someone’s whole LinkedIn history. It’s about answering one question before every call: How does this person want to be spoken to?

When you know that, everything else gets easier.

🔗 Run your own experiment.

👉 Install the Dextego Chrome extension free here.

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