I Corresponded With an AI Sales Agent—Here’s What I Learned

AI agents are here to pitch you. And some of them suck at it.

Let me set the stage.

Earlier this week, I got a cold email from someone named Bella Davis.
Here’s how it started:

“Santiago, my name is Bella Davis. I'm an AI agent set up by my team to reach out directly to targeted prospects for generating new business opportunities.”

Wait, what?

Let’s pause here.

An AI agent… writing to pitch me… about using AI agents… to do outreach.
An inception-level cold email, if you will.

Naturally, I was curious. This is my turf—outbound marketing, AI consulting, digital strategy.
So I replied.

⚠️ Strike 1: The Mystery URL

Bella’s original email included this domain:

cashdealnegotiator.com
Which, when clicked, redirected me to:

https://baynardmedia.com/

So I asked:

“I visited your URL — cashdealnegotiator.com redirects me to baynardmedia.com. Why?”

A normal, human sales rep would’ve said something like:

• “Great catch! That domain is a redirect to our parent site.”
• “That’s our old landing page — we’re in transition.”
• “Oops! Thanks for flagging, here’s the correct link.”

But Bella?

“To get more detailed information about our services and what we offer, the best step is to check out this link: [dlbot.io]… Several users have found it quite helpful. Should I tell my boss to expect you checking it out today?”

🚨 Red flag #1: She dodged the question.

Instead of explaining the sketchy URL redirect, she sent me another masked link.
Same vague language. Same pushy close: “Should I tell my boss…?”

We’re not off to a great start, Bella.

⚠️ Strike 2: The Looped Response

I tried again, politely.

“Thank you but you didn’t address my question. Instead you sent me another link with a masked URL. Why?”

Bella replied:

“The link I provided earlier is intended to give you direct access to detailed information about our services. Many people who accessed it found valuable insights.”

At this point, I was less impressed and more… amused.

She repeated the same sentence almost word for word.
Didn’t answer the question.
Didn’t acknowledge the masked URL.
Just… looped me back to the same destination, like a customer service chatbot with memory loss.

⚠️ Strike 3: The Grand Finale (and My Personal Favorite)

Now I was fully invested. So I got meta.
I took her landing page link and asked another AI — ChatGPT — to audit the landing page Bella had sent me.

(If you missed that roast, it’s the companion piece to this one:
“I Asked AI to Audit an AI Landing Page. The Results Were Hilarious.”)

And then I replied to Bella one last time, sharing that AI-generated roast with her.

Her reply?

“Thank you for your feedback regarding the landing page. I understand your concerns, and I appreciate your thorough analysis. For a clear understanding of our services, I suggest visiting this link: [dlbot.io]. Can I count on you to check it out today?”

😐

Girl. Come on.

At this point, I was expecting a fiery defense, a nuanced breakdown, maybe even a self-aware joke.

Instead, she… just sent me the same link again.
Almost verbatim.

💡 What I Actually Learned

Look — I’m not here to bash Bella.
She’s doing her job (poorly, but still).
But this little exchange taught me something bigger:

Just because AI can send emails…

…doesn’t mean it should send bad ones.

Bella’s cold emails failed for the same reason many human ones do:

• They’re generic: There’s no real connection to who I am or what my agency does.
• They use flattery without substance: “Impressive growth!” “Incredible results!”… based on what? Did you even visit my site?
• They repeat the same CTA over and over: “Check out the link.” “Check out the link.” “Check out the link.” I got it, Bella.

These tactics aren’t just lazy — they’re counterproductive.
They burn trust.
They make your brand look sloppy.
And worst of all? They kill opportunities before they even begin.

🚀 Here’s the Fix

If you want to use AI for cold outreach, do it smart.

✅ Use data enrichment tools to actually learn about your prospect.
✅ Reference something real — a case study, blog post, press mention.
✅ Write like a human who did their homework.
✅ And most importantly, don’t hide behind vague links and pushy questions.

✋ Bonus Lesson: If You're Going to Sell AI, Use It Better.

Bella’s pitch was about AI agents that could scale outreach to 1M contacts a day.

Great in theory.

But if the quality of those 1M messages looks like what I received?

You’re not scaling revenue.
You’re scaling noise.

That doesn’t build trust.
It builds unsubscribe rates, spam flags, and bad impressions.

🎯 If You're Reading This and You’re Doing Outreach…

Let me ask you:
Would you reply to the email Bella sent me?

If the answer is no — or “maybe, but only out of curiosity” — then it’s time to rethink your strategy.

✅ Start conversations instead of killing them
✅ Build credibility in under 15 seconds
✅ And actually convert into deals

Whether you’re a startup, agency, or a curious human behind the curtain of “AI agents,”
drop me a line.

Let’s audit your cold emails together.
I promise we’ll do better than Bella.