still chasing big logos?

This Week in the Trenches: The Enterprise Trap

This week, three different founders asked me the same thing:

“Should we be targeting enterprise?”

And every time, my answer was the same:

Only if you want 0% reply rates and your domain flagged into oblivion.

Here’s the brutal truth no one wants to say out loud:

Mass cold outbound doesn’t work on enterprise.
Not anymore.

And the more you chase big logos, the worse your pipeline gets.

Let me break it down.

Enterprise inboxes are built to block you.

It’s not just that they have stronger spam filters.
It’s that they’re actively trained to reject volume.

These systems don’t care how clever your copy is.
They’re watching patterns.

• Multiple emails from new domains? Flagged

• Identical messaging across accounts? Flagged

• Cold infrastructure with weak SPF/DMARC? Blocked

• Personalised icebreakers with no signal? Ignored

Even if you land, you're landing in a fortress:

• Gatekeepers shielding decision-makers

• Legal and procurement red tape

• Multi-threaded, multi-month sales cycles

You're not just trying to start a conversation.
You're trying to hack through six layers of bureaucracy before you even qualify the deal.

So why do founders keep going after enterprise?

One word: ego.

Big logos look good on slide decks.
“Six-figure ACV” sounds better than “20 mid-market deals.”

But here’s the thing.

Outbound isn’t brand marketing.
It’s interruption marketing.

And interruption only works when:

• The pain is real

• The prospect has power

• The process to buy is simple

Enterprise fails on all three.

The best campaigns we’ve run this year had one thing in common:
Mid-market targeting.

Not sexy. But effective.

Here’s why:

• The CTO reads their own email

• The founder still runs sales

• The pain is urgent and felt directly

• The deal cycle is short enough to close in weeks, not quarters

And most importantly?

Your emails actually land.

You’re not fighting Google’s enterprise-grade filters.
You’re landing in Gmail inboxes that still have air.

To be clear, I’m not saying you should never sell to enterprise.

I’m saying cold email isn’t the way in.

If you're serious about that market, here’s what works:

• Social selling to build familiarity over time

• Signal-based targeting (job changes, tech shifts, intent)

• ABM-style content and outbound, tailored and slow

• Phone and referrals, not just inbox blitzes

Enterprise requires precision, not volume.
Timing, not templates.
Relationships, not just replies.

So here’s the reframe.

Stop asking “how do we move upmarket?”
Start asking “how do we win efficiently?”

The answer probably isn’t Fortune 500s.
It’s that $10–100M ARR company with clear pain and no internal politics.

They still buy fast.
They still read cold emails.
And if your system is tight, you can book them like clockwork.

Tom