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How I’d Improve an AI-Powered Cold Email (That Felt Personally Insulting)

Photo by Joni Ludlow on Unsplash

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Got an AI-powered cold email today for an AI service. It was terrible. 🤖 👎

The copywriting, the personalization, all of it.

Sad thing is that when used right, AI copywriting can enhance outreach in a major way. Here’s how I would rewrite their AI pitch template and why I think it’s an improvement.

The Pitch Itself… Wasn’t a Great Demo of AI Copywriting

Here’s their pitch (name and company info redacted to not be uneccessarily mean):

Yes, it literally cuts off in the last line after “Have a”.

I’d assume they meant, “Have a big kick in your face,” because this email makes it clear that’s how much respect they have for me.

Or maybe it was, “Have a full pizza to yourself, just as a little treat this evening, because you deserve it.” That would make as much sense as some of their other “personalizations.”

How Did This Happen, Anyway?

The irony of all this is that the email, itself, is a sort of sales pitch for AI copywriting.

The CTA link went through, which says it “lands new customer meetings by sourcing and engaging from 340m+ ideal customer profiles.”

In normal speak, that means, “We built software that crawls every social profile possible, then uses AI to spam them.

Even their marketing site implies this is the case. Just look at this graphic from their homepage gif*

Screenshot from a marketing page for an ai powered spam service
(*Bonus snark: why are they using a 9.1 MB gif on their homepage when an optimized video file would be only 2 MB? Yes, I converted and optimized it just to check. And no, I’m not going to give it to them.)

Yes, you’re reading that right. They’re pitching a cold outreach tool that surfaces tens of thousands of contacts at a time.

They’re getting around spam laws by technically sending each email one at a time.

But in practice and intent, this is spam. It’s uninvited, unwanted email communications that add no value to my life.

Good outreach focuses on relationship building and respect. This is arguably not good outreach. Let’s run some numbers as proof.

  1. You decide to send 23,500 AI-generated emails to contacts scraped from the web. And let’s assume it’s a really good outreach email that gets a 10% cold response rate. That’s 2,350 people who said, “Sure, I’ll know more.”
  2. You’re now responsible for responding to over two thousand people in a timely manner; otherwise, the leads will go cold. Assuming it’s a 15-minute phone call per lead, that’s 587.5 HOURS of phone calls.
  3. How long would it take you to make 587.5 hours of high-energy sales calls? Even if you’re incredibly talented, and somehow your calls end at 15 minutes flat, that’s 14 weeks or 3 MONTHS of back-to-back calls, all day, every day.

Sounds like hell. (And not just for the people receiving the sales calls.)

Those numbers represent the most ethical version of this outreach scale, where the outreach email is good. But if the example that reached my inbox is any indication, their response rates are far, far lower – maybe 0.5% at best.

That means that spamming 23,500 people ends up with a more manageable 117 people responding.

But think about that: you’re taking enough people to populate a city, and ending up with only a very poorly attended trade show. That’s spam.

So now we’ve established why this approach is fundamentally flawed as its being presented. But this isn’t just a dunk session, it’s an educational opportunity.

Breaking Down Why This Pitch Doesn’t Work

By looking at the elements of a good cold outreach email, we can see why this AI-generated abomination fell flat.

A good cold outreach email needs to be:

  • Well-targeted: An outreach campaign is like going out to forage for food. You’re looking for something specific. (In this case, it’s a person who fits your well-defined, specific ideal customer profile.)
  • Personal: I don’t know anyone who likes to receive a broadcast email clearly intended for as many people as possible. Email should be treated like a personal, one-to-one medium.
  • Relevant: If the goal of the email is to drive sales calls, the offer needs to appeal to the individuals receving them.
  • Appropriately-sized: How big is your ask?
  • Surprising (in a good way): Cold outreach is a great way to surprise someone with the solution to the problem they didn’t know existed. You want them to say, “Oh wow, I could actually use this.”

If this looks like a lot of work, it should be.

The pitch I recieved was not a lot of work. It was lazy right from the get-go.

Their hook:

“Hi Matt — I hope you are having a nice quarter. I’m inviting people with similar backgrounds to an exclusive session below.”

Okay, my similar to my background in…??? You mean boring, middle-aged dads? White dudes with beards? Or do you mean something related to my work?’

The (non) personalization: “I like that Common People Web Design is into user experience.”

This comes across as hilariously incompetent. First, you “like” that our web design studio does… the thing that we do? How revolutionary. 🙄

The next part is somehow less insightful.

“I was reading that it [user experience] will be very important in 2022 and beyond. So, I thought I’d share my thoughts on it with you. It was a good read.”

Just… I mean… I can’t… why would you write this and think it was acceptable?

Let me get this straight: you read an article stating that user experience – which is, like, huge – is going to be important in the coming year? And it was a “good read”? This is about as articulate as Detective Crashmore (warning: language).

This lazy, “not even good enough for a first draft” copy isn’t just completely devoid of value, it’s also awkward.

At this point, we finally get the introduction and call to action:

“I’m [NAME], [TITLE] at [COMPANY]. Please accept our invitation for an exclusive session (attached deck here), to learn more about how we’ve helped companies similar to yours.”

So the ask isn’t, “Do you want to see the article I thought was valuable?”. It’s, “Click this tracking link to watch a ‘session’ of an indeterminant topic and length.”

literally don’t know what the session is about. Is it a pitch for a timeshare? Are they trying to get me to join their downline? Is it a live meeting, or a recording?

All I know is that it’s about how they’ve “helped companies similar to [mine]”. So far, I’ve seen a complete lack of evidence that they know anything about me (although this will change in a creepy way very soon). And I have no idea what they do, let alone what they can do for me.

Finally, the email comes to an merciful end… but not before ramping the creep factor up to 11.

“Btw, if you were in the Los Alamitos area, the forecast says it’s drizzle today. Have a   “

Two observations about this:

  1. Yes, the email just stops mid-sentence. “Have a     ” is indeed how this trainwreck ends.
  2. My website says our business is located in Long Beach, not Los Alamitos. But my home address is in Los Alamitos. So that’s creepy.

Personalization can show you care. But creepy, invasive levels of personalization show you care too much (or not enough).

So the email is over, and to recap:

  • They don’t include enough information about whether or not the email is targeted at me
  • The email contains some personal info, but not the right kind of personal info
  • Because it’s so vague, the email isn’t relevant to me in any meaningful way
  • The ask is ambiguous, and as a millennial who’s spent my entire adult life avoiding spam phone calls, I don’t even answer the phone unless I’m specifically expecting a call – no, I’m not clicking that
  • The email surprised me, but in a “guess I have to write 2200 words on cold pitching today” kind of way, not the “pleasant surprise” way they intended

A bad, bad pitch.

A Quick Note about the Footer

The footer of this spam email contains a soft pitch for the service used to serve this atrocity.

You can respond ‘STOP’ to opt-out of this company. Kalendar AI has written the content in this email for our customers. If you see any errors in the content generation, please report them by responding to this email to us with your kind, big heart. We are helping businesses connect, and small businesses thrive. We respect your privacy by processing publicly available information and don’t store any personal information in full compliance with CCPA, GDPR, and CAN-SPAM acts. You can also opt-out of our data processing. Sent by Kriya Inc, located at 1592 Union St, San Francisco, CA 94123.

Again, they almost explicitly acknowledge their business model relies on navigating around spam laws.

Not a great look.

What Does a Good Pitch Look Like?

Look, I could write an entire article rehashing how to do good cold outreach. But smarter people than me like Amanda Natividad at SparkToro and Bree Weber at Cold Pitch Copy.

So go read their words and come back.

Let’s Rewrite This Pitch

“Hey [NAME], I’m reaching out to leaders doing awesome work in the [INDUSTRY-SHORT] space. Love what you’re doing at [COMPANY]. I stumbled across an article about [INDUSTRY-MEDIUM] in 2022 and would love to know your thoughts. Want to check it out? [LINK TO INDUSTRY-SPECIFIC CONTENT].

PS: are you in [LOCATION-REGION]? Looks like a [WEATHER] day there – [WEATHER-SPECIFIC GREETING]!”

So after being parsed with AI, it might look something like this:

“Hey Matt, I’m reaching out to leaders doing awesome work in the UX space. Love what you’re doing at Common People. I stumbled across an article about UX design in 2022 and would love to know your thoughts. Want to check it out? [Link]”

“PS: are you in Southern California? Looks like a rainy day there – stay warm and dry!”


🤖 First, it’s shorter and wastes less of my time. So I’m not immediately annoyed/put into a negative emotional space by it.

🤖 Second, even though it’s shorter, it feels more relevant (or less irrelevant) to me. It’s also more flattering (“I’m a leader doing awesome work? Little ol’ me???”), which makes me emotionally more receptive to whatever the ask is.

🤖 Finally, the ask in this version feels like a favor from a friend, not spam. Since we’re using AI-powered outreach, why are we still thinking in outdated models of scale?

If AI lets you personalize first-stage outreach at new scales, why not additional stages?

As the brilliant Bree Weber teaches, cold pitching is a process, not an event. Build a relationship and add value to make better pitches.

AI will be an AWESOME tool that will free us to focus on strategy and human connections, not the gruntwork of typing. But we have to give a damn and not use it for deeply off-putting spam.

Let’s think bigger about how tech can enable human, deeper connections at unprecedented scale.

And please, PLEASE remember that it’s always a human being whose eyeballs 👀 are reading your emails. Respect their humanity, and don’t ruin your business’s reputation with careless spam.

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