Launching “Command The Cycle” this Tuesday.
7 months in the works… or 7 years…
Everyone says you need to build pipe. Strong discovery. Great negotiation.
But one things that’s always separated top performers is all the “off the call” work.
How you prep, stay top of mind between meetings, follow up memorably, strategically drive towards value add next steps, identify compelling events, create work back plans, and more.
118 pages. No Fluff.

NEWS TO KNOW

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📚 – A Top AE’s Favorite 12 Discovery Questions​
📝 – Cold Calling Strategy… for a New Job​
💸 – 90 Days Until 2026…

CONTENT OF THE WEEK

Reframing ROI Conversations with the CFO

Here’s the thing about CFOs: they’re not sitting around waiting to write checks.

They’re actively looking for reasons NOT to buy your solution.

Last year, our CFO walked our sales team through exactly how purchase decisions get made.

What he shared was eye-opening.

Instead of trying to convince him why something was worth buying, he was systematically hunting for ways to disqualify the investment entirely.

This changes everything about how you should approach ROI conversations.

The CFO’s Playbook

Here’s what our CFO actually looks for when evaluating any technology investment:

The Four Pillars Test:

1. Does this align with our existing company objectives for the year?
2. Does this reduce costs, grow revenue, or reduce critical risk (compliance/security)?
3. Can we do this internally instead?
4. Have we looked at other alternatives?

The Timing Challenge:

1. Do we really need this now or can it wait?
2. What’s the actual ROI?

The Budget Reality:

1. Who built this ROI model – you or us?
2. Is there open budget for this? If not, what are we willing to cut?
3. How will costs change over time?

Notice something? Six of those nine questions are designed to kill the deal, not approve it.

The Cost of Inaction Framework

Instead of starting with benefits, start with consequences.

CFOs understand risk better than they understand opportunity.

Frame it like this:

“Let me walk you through what happens if we don’t solve this problem in the next 6 months…”

Then use this three-part structure:

1. Current State Costs Quantify what the problem is costing right now. Be specific.

Example: “Your customer service team is spending 14 hours per week on manual data entry. At $65k average salary, that’s $23,400 in wasted labor annually just from this one process.”

2. Escalation Costs Show how the problem compounds over time.

Example: “As you add 200 new customers per quarter, this manual process will require an additional full-time hire by Q3. That’s $65k in salary plus benefits, bringing total cost to $95k annually.”

3. Opportunity Costs Connect to strategic objectives.

Example: “While your team handles data entry, they can’t focus on the proactive customer success initiatives in your Q2 objectives. Each delayed implementation costs you an estimated $40k in potential upsell revenue.”

Tactical Conversation Starters

Instead of: “Our solution provides 300% ROI”

Try: “What’s it costing you to not have real-time visibility into your pipeline right now?”

Instead of: “Here are all the features you’ll love”

Try: “Walk me through what happens when your current system goes down for maintenance”

Instead of: “This will save you time”

Try: “How much revenue opportunity are you missing while your team spends 2 hours daily on manual reporting?”

The Internal Champion Leverage

Remember question #7?

CFOs trust internal ROI models way more than vendor-provided ones.

Your job isn’t to build the business case.

It’s to equip your champion with the framework to build their own.

Here’s the reality: the CFO isn’t going to review your 22-slide business case deck. They’re not going to sit through your ROI presentation.

That conversation happens internally, without you in the room.

Your champion walks in with a 2-page summary and gets 10 minutes to make the case.

If your champion can’t defend the numbers when the CFO asks tough questions, you lose. This is why co-building the business case with your internal champion is critical.

They need to own every assumption, understand every calculation, and confidently defend the logic.

The Budget Trade-Off Question

Here’s the most revealing question from that list: “What are you willing to cut to make budget for this?”

Their answer tells you everything about their conviction level.

If they can’t name specific trade-offs, the deal isn’t real yet.

Use this: “If your CFO said we don’t have the budget… what tradeoffs would you be willing to make. How would you answer?”

Their response will either strengthen the urgency or reveal you need to keep building value.

The bottom line? Stop trying to convince CFOs to buy.

Instead, help them understand the true cost of not acting.

They’re already looking for ways to say no.

Make the cost of “no” impossible to ignore.

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Win the week!!!