Hey Niepodam,

A CRO told me: “Can you review our outbound? It’s not converting.”

I asked one question: “Does any of it make the buyer slightly uncomfortable?”

Silence. That’s the issue.

Most SaaS outbound is engineered to be safe.

• Safe messaging.
• Safe assumptions.
• Safe CTAs.

But complex B2B deals don’t move because something feels safe.

They move because something feels exposed.

Enterprise deals hate friction

That’s the myth.

Everyone says, “Make it easy for the buyer.”

Sure. Operationally.

But strategically?

You NEED friction.

• Because friction creates awareness.
• Awareness creates urgency.
• Urgency creates movement.

If your message doesn’t disrupt the buyer’s current narrative, you’re just background noise.

Radical outbound introduces productive discomfort

When I work with reps selling into multi-threaded enterprise accounts, we flip one thing:

We stop asking for time.
We start challenging assumptions.

Instead of: “Would love to show you how we help companies like yours.”

Try: “Most teams at your stage think their process is ‘good enough.’ Then Q3 exposes the cracks. Curious — where do yours usually show up?”

That line does two things:

• It challenges their self-perception.
• It predicts a future problem.

That’s tension.

And tension gets replies.

Complex deals require narrative control

In SMB, interest + timing are enough.

In enterprise, you’re competing against:

• Budget cycles
• Internal politics
• Competing priorities
• Executive ego

Radical outbound isn’t about volume.

It’s about controlling the narrative early.

On first calls, I’ll say: “If this becomes a real initiative, what would have to be true internally?”

Now we’re talking about mobilization, not features.

Later, when deals slow down, I don’t “check in.”

I re-anchor the stakes: “When initiatives like this stall, it’s usually because the business case isn’t strong enough for Finance. Do we need to sharpen that together?”

I’m not waiting. I’m steering.

Momentum > Meetings

Here’s the shift most SaaS teams miss:

Meetings don’t create pipeline.

Momentum does.

Momentum looks like:

• Clear next step with a date
• Named stakeholders
• Agreed business problem
• Defined impact

If your outbound doesn’t set up those four things from the first touch, you’re just scheduling conversations.

Not advancing deals.

A simple radical structure

When building outbound into complex accounts, I use this structure:

1. Call out the blind spot: “Teams scaling past $X usually underestimate Y.”
2. Quantify the cost of inaction: “That typically shows up as Z — lost revenue, delays, churn.”
3. Expand the lens: “This tends to touch Sales, Finance, and Ops.”
4. Propose a forward motion step: “Worth pressure-testing whether this is a Q2 fix or a 2027 regret?”

Notice what’s missing?

No begging.
No “just checking.”
No soft language.

Radical outbound isn’t louder.

It’s sharper.

It creates tension.
It builds internal gravity.
It forces a decision.

In complex deals, your job isn’t to be liked.

It’s to make standing still uncomfortable.

Alan "Modern Seller" Ruchtein.

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