Hey Niepodam,

3 months ago, we were trying to sell a fintech platform to CFOs.

• $60K average contract.
• 3 stakeholders minimum.
• Finance. Ops. IT.

Outbound wasn’t the issue.

Meetings weren’t even the issue.

Deals were stalling after the first call.

Why? Because we were selling like it was a single-threaded SaaS tool.

It wasn’t. It was a political decision.

And CFOs don’t buy tools.

They buy risk reduction.

That’s when we built what I call the CFO Triangle Sequence.

Radical. Simple. Brutally effective.

The Problem With “Normal” Sequences

Most reps do this:

• Email CFO
• Follow up 6 times
• Maybe loop in Ops later
• Hope internal alignment happens magically

It doesn’t.

In $60K fintech deals, the CFO is the economic buyer.

But they won’t champion something that creates internal friction.

So instead of chasing the CFO…

We orchestrated the triangle from day one.

The CFO Triangle: 3-Step Outbound Sequence

Step 1: Disarm The CFO (Risk-First Outreach)

Forget ROI. CFOs assume every tool promises ROI.

Lead with exposure.

Email example:

“Mark — quick question.

When finance teams evaluate new payment infrastructure, the biggest hesitation I hear isn’t cost.

It’s implementation risk + audit exposure.

How are you pressure-testing new vendors this year?”

No demo ask.
No deck.
No features.

You position yourself inside their risk lens.

CFOs reply to risk conversations.

Not shiny objects.

Step 2: Parallel Path The Operator

Within 48 hours, we reach out to the operational stakeholder (Head of Finance Ops or Controller).

Different angle.

Email example:

“Anna — when teams move off legacy payment workflows, the friction usually shows up in reconciliation and reporting.

Before leadership makes any decision, what would need to be true operationally for this to work?”

Notice what we’re doing? We’re not asking for a meeting.

We’re mapping landmines.

Now if Anna replies, we know the internal blockers.

If she doesn’t, but CFO does, we bring her up on the call strategically.

Step 3: Pre-Sell IT Before IT Blocks You

This is where most fintech deals die.

• Security review.
• Integration concerns.
• Data residency.

So we proactively send this to the IT lead:

“David — looping you in early because in similar evaluations, security + integration become the gating items late in the process.

Happy to send over our architecture overview and get ahead of any red flags before this becomes urgent internally.”

No pressure.

Just de-risking.

Now when the CFO asks IT internally, you’re not a surprise.

You’re expected.

Why This Works

Because enterprise fintech isn’t persuasion.

It’s orchestration.

CFO cares about:

• Financial risk
• Vendor stability
• Audit exposure

Ops cares about:

• Workflow disruption
• Reporting accuracy
• Team workload

IT cares about:

• Security
• Integration
• Compliance

Three different fears.

One deal.

Most reps pitch one story to all three.

That’s lazy.

The Tactical Breakdown

Here’s the sequencing:

Day 1: CFO risk email
Day 3: Ops friction email
Day 4: IT pre-emptive de-risk email
Day 6: CFO follow-up referencing cross-functional alignment

Follow-up example:

“Mark — when we’ve done this successfully, finance, ops, and IT align early so nothing stalls in procurement.

If it makes sense, happy to walk through how other CFOs structured that internally.”

Now you’re not selling software. You’re selling internal alignment.

That’s worth $60K all day.

The Real Takeaway

In multi-stakeholder deals:

Don’t chase one champion.

Build the triangle before the first meeting.

When alignment happens before procurement…

Your close rate jumps.
Your sales cycle shrinks.
And you stop getting ghosted after “This looks interesting.”

Want me helping you and your team within your sales efforts? Let’s talk.

Or book me here directly for a Free Strategy Call

Alan "Modern Seller" Ruchtein.

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