Hey Niepodam,

If you're selling into Enterprise and your cold emails aren't landing, it's probably not your product.

It’s your approach.

Enterprise leaders don’t think, act, or reply like mid-market buyers.

They don’t have time for “just checking in.”They don’t care about features.
And they definitely don’t click Calendly links from strangers.

They don’t have time for “just checking in.” They don’t care about features.

And they definitely don’t click Calendly links from strangers.

Here are the 4 biggest mistakes I see reps make in Enterprise cold emails—and what to do instead.

1. They sound like SDR templates.

“Hi [First Name], I noticed you're hiring and wanted to reach out…”

The second an Enterprise buyer sees “noticed you're hiring,” they tune out.

Why? Because that same line showed up in 8 other emails today.

Fix it: Start with a sharp POV, not a generic signal.

“Most Heads of CX I speak with are buried in support backlogs and exec pressure to improve CSAT—sound familiar?”

Now you’ve got their attention.

2. They pitch way too soon.

Enterprise buyers don’t respond to pitches, they respond to problems they care about.

Bad email: “We help companies like X and Y do Z. Would love to connect!”

Fix it: Lead with a problem, not your solution.

“Quick Q, how are you prioritizing which customer issues get escalated to Tier 2? A few teams I’ve spoken with are seeing response times ballooning because of poor triage rules.”

That’s how you open a conversation, not a pitch.

3. They don’t show their homework.

Enterprise buyers expect sellers to already know the basics.

Bad email: “I saw you’re the VP of Ops at Acme…”

Congrats, you can use LinkedIn. That’s not personalization. That’s filler.

Fix it: Use relevant context that proves you understand their world.

“Saw your recent comment on [podcast/article] about scaling onboarding. Curious, are you leaning more toward in-house or third-party tooling for that?”

Real research beats fake flattery every time.

4. They go too small.

Enterprise buyers aren’t looking to fix minor pains.

They care about strategic initiatives, not point solutions.

Fix it: Frame your email around business impact.

“Teams using [our category] are seeing 10–15% faster ramp for new reps, and that’s unlocking 7 figures in ARR impact within 12 months. Should we unpack if there’s a fit on your side?”

That’s big. That’s boardroom language.

Want your reps writing emails that Enterprise leaders actually respond to?

We can cover this inside the Modern Seller Coaching Program.