B2B discovery call qualifying questions: ask about CAC and sales team size

Sunny Ray · Sep 19, 2026 · 6 min read

If you sell to founders, two discovery questions tell you more about fit than any other: what is your customer acquisition cost, and how big is your sales team? CAC tells you what a new customer is worth to them and whether they can pay for help getting more. Sales team size tells you who you are really talking to and who signs. Ask both early, and you stop spending weeks on deals that were never going to close.

We added both to our qualifying flow on September 15. On the same call we changed one habit that was quietly killing deals: we started getting the other co-founder on the call.

Why CAC tells you fit

Customer acquisition cost is the clearest signal of whether a founder values a new customer enough to pay for one.

If their CAC is very low, they are probably not a fit for us. Either their deals are small, or they already have a cheap channel that works, and in both cases paying for a system that books meetings with senior buyers will feel expensive. Nothing wrong with them. It is just not the right conversation.

If they do not know their CAC, that is a signal too. It usually means growth so far has come from the founder’s network and nobody has had to count what a customer costs. Those founders can be great clients, but the conversation starts somewhere else: what is a customer worth to you, and what would you pay to get ten more?

And if they know it and it is high, you are talking to someone who already understands that customers cost money, and who can tell you in one number whether your offer pays back.

That is why CAC is the best fit question I know. It reveals lead value and fit at the same time.

What sales team size tells you

The second question is how many people are on the sales team.

If there is a team, there is probably a CRO or a VP of Sales. That person often owns the budget for what you sell, or at least has a strong say. If you are only talking to the founder, you need to know whether there is someone else you should be talking to.

If there is no sales team, you are talking to the decision-maker, because the founder is the sales team. That is good news for speed. It also means their time is the constraint, and your offer has to save it.

Either answer is useful. What you cannot afford is to not know.

The missing co-founder problem

The bigger fix from that call was not a question. It was a habit.

We had deals stalling for the same reason over and over. A founder would love the call, love the offer, say they needed to talk to their co-founder, and then nothing. The co-founder had never been on a call. They had heard about us second-hand, filtered through someone else’s excitement, with none of the context.

Charles’s view was simple. Decisions between co-founders are usually 50/50, and pitching through one founder to the other rarely works. So he started inviting the co-founders directly onto calls. The early results were positive.

It sounds obvious written down. In practice most founders selling to other founders accept “let me check with my partner” and wait. Waiting is how good deals die.

Getting the second decision-maker in the room

Inviting the co-founder to the sales call is one route. A day earlier, on a separate call, Charles and I had compared notes on another.

We had tried inviting the second partner onto the podcast itself. It did not work reliably. Introverted partners do not always want to show up for a recording. So we switched: invite the second partner to the debrief instead. The debrief is the business conversation after the taping, smaller and more private, and much easier to say yes to.

So the playbook now looks like this:

• Ask early whether anyone else is involved in the decision.
• If there is a co-founder or partner, invite them directly, by name, to the next call.
• If they will not come on the show, invite them to the debrief.
• Do not pitch through one founder to another and hope.

Ask it inside the interview

If you run a show, a lot of discovery happens before anyone calls it discovery. The questions we suggest asking on the record map neatly onto qualification:

• “What are you building, and where are you in it?” tells you fit.
• “What’s the hardest part right now?” tells you need.
• “What have you already tried?” tells you budget, and what they have already spent money on.
• “What happens if nothing changes this year?” tells you timeline.
• “Who else weighs in on a call like that?” tells you authority.

On a sales call the prospect runs the clock. In an interview you do, and they leave feeling listened to, not worked. By the time you get to CAC and sales team size in the debrief, you already know most of the answer.

Stay flat on the call

One more thing Charles and I compared notes on in mid-September: the closes that surprised us most came from not trying too hard. A casual catch-up turned into a yes. A low-pressure call closed faster than a formal pitch. Charles calls it managing your cortisol: stay flat, do not spike on good news or bad. Discovery questions work best asked with genuine curiosity, by someone who does not need the answer to be yes.

Where these questions go

Some of this belongs on the booking page and some belongs on the call. CAC can go either way. A booking form can ask it, and if they skip it or say they do not know, you have learned something before the call starts. Sales team size is an easy booking-page question. The co-founder question is best asked live, early, in a natural way: who else will weigh in on something like this?

The point of all of it is to spend your time on the conversations that can close, with the people who can close them.

The questions, in one place

1. What does it cost you to acquire a customer today?
2. How many people are on your sales team?
3. Who else weighs in on a decision like this?
4. Can we get them on the next call?

Run your own numbers

If you are a founder reading this from the other side, ask yourself the first question before anyone else does. What does a customer cost you, and what is one worth? If you know both, you can decide in a minute whether a show that books buyers onto your calendar pays back, and in which month. Our ROI calculator does that math with your numbers: payback month, return per dollar and cost per client won.

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