Everyone Gets Personalization Wrong

If your version of personalization looks like this:

“Hey {{FirstName}}, saw your Bali pics 🌴 — anyway, here’s why you should check out our product…”

then you’re not personalizing.
You’re being creepy.

Somewhere along the way, “personalization” became synonymous with “how good are you at stalking.”
And the result?
Emails that sound more like awkward small talk than genuine outreach.

We’ve all seen it — forced attempts at “relating,” superficial name drops, or random facts pulled from social media.
That’s not personalization.
That’s desperation in a mail merge.

Let’s fix that.

The Real Meaning of Personalization

Personalization isn’t about what you know about someone.
It’s about how well you understand them.

It’s not:

“I know you went to Bali.”

It’s:

“I know your team is scaling fast and probably drowning in manual vendor reviews.”

That’s relevance.
That’s respect.

And that’s what people reply to.

So, instead of forcing your email to sound “personal,” make it relevant.
Here’s how.

1️⃣ Using Personal Info (Lightly)

Personal info isn’t the villain.
It just needs to be used with self-awareness and a bit of humor.

If you’re going to use it, treat it as a pattern interrupt, not the centerpiece of your pitch.

Example 1:

“Saw your Bali post — that water looked criminally blue.
Keeping envy aside… quick question on how your team handles vendor reviews?”

Example 2:

“P.S.: Saw your team’s 5k run.
I get tired just watching. Someday, {{sender_name}}, someday.”

That’s the right kind of personal.
It’s human, warm, a little witty — but not weird.

It makes the reader smile, not squirm.
Then it gets to the point.

2️⃣ Their Role & Their World

If you do only one kind of personalization, do this one.
Because this is where real understanding lives.

Every role comes with its own set of challenges.
Show you get that — and your email will instantly feel more thoughtful.

Example:

“As a Head of RevOps, how much of your week goes into fixing CRM sync issues?
Most teams we work with cut that time by half.”

Notice what’s happening here?
You’re not pitching a product.
You’re reflecting their world back to them.
You’re saying, “I get what your life looks like.”

That’s empathy disguised as personalization.

3️⃣ Their Company

“Personal” doesn’t always mean about them.
It can mean about their company.

If you’ve read their quarterly report, press release, or even a blog post — mention it.
Show them you’re tuned in to what matters to their org.

Example:

“Read your Q2 report — saw the push toward digital transformation.
We helped another BFSI team automate 80% of manual checks during a similar phase.”

That’s personalization done right.
No flattery. No filler.
Just clear evidence that you did your homework.

It tells the reader:

“You’re not just another name on a list.”

4️⃣ Their Tools & Tech Stack

Mentioning their stack is a simple but powerful way to signal relevance.
It says: “I understand how your team operates — and I’ve thought about how this fits in.”

Example:

“Noticed you’re on HubSpot + Slack.
Our workflow plugs right in, so reps can update deals without leaving Slack.”

See what happened there?
You didn’t list integrations.
You explained why that matters to them.

That’s what separates real personalization from lazy automation.

5️⃣ Timing & Triggers

Sometimes, the best personalization has nothing to do with the person or company — it’s about when you reach out.

Trigger events like fundraising, product launches, or leadership changes are gold.
They give you natural context and perfect timing.

Example:

“Congrats on the Series B 🎉
That kind of growth usually means more vendor security reviews.
We help teams handle those automatically.”

That email feels timely, thoughtful, and useful — not robotic.

Timing is personalization.

The New Twist: Personalization in the Age of AI SDRs 🤖

Here’s where it gets interesting.
AI can now research faster, summarize better, and even write cleaner than most humans.
But AI can’t care.

And personalization, at its core, is an act of caring.

It’s ironic — we’re now training machines to sound human.
But the real personalization doesn’t happen in the email the AI writes.
It happens in the inputs you give it.

If you feed your AI SDR the wrong data — “pull 3 random facts from their LinkedIn” —
you’ll get creepy personalization at scale.

But if you feed it good data — their role, company focus, stack, and current priorities —
you’ll get personalization that actually resonates.

So the question isn’t,

“Can AI personalize?”
It’s,
“Do you care enough to teach it how to?”

AI doesn’t replace personalization.
It scales it.
And the personal part now lives in how much you care about setting it up right.

TL;DR

Personalization isn’t flattery.
It’s not trivia.
It’s not knowing their dog’s name.

It’s effort + empathy + timing.

It’s about showing you understand their world —
their role, their company, their goals —
and that your message actually belongs in their inbox.

So next time you write a cold email, skip the Bali line.
Or at least, if you mention it, make it funny.
Then pivot to something that shows you get them.

Because the best personalization doesn’t make someone say,

“Wow, how did they find that out?”

It makes them say,

“Yeah, that’s exactly what I’ve been dealing with.”

That’s real personalization.

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