The two key questions to ask B2B SaaS Positioning

Your value prop pillars make you stand out. They should be the one, two, or few thighs you do that nobody else does. A common mistake that some B2B SaaS companies and marketers make when looking at value proposition pillars is how many they need to have.

The other day we were talking with a new client of ours and they had come in with some positioning exercises they had done before. One of the exercises was for value proposition pillars. It was an excel sheet of 14 different tabs. Each tab with a value proposition and then the reasons to believe it. That was for only one industry. For one very specific ICP.

It wasn’t for features; it wasn’t necessarily for benefits, the way you’d think of them, just 14 different value props. The reasons to believe each was the same were because there were too many of them. Then, of course, we did a positioning exercise together, narrowed it down to what makes them stand out, and mapped them with their personas, but this reminded me of something I learned way back in debate club.

What is the first rule of a debate club?

Don’t list all your arguments. If you have multiple arguments to make in debate club, the worst thing you can do as a debater is list four or five arguments. Why? Because your opponent then will take your weakest argument and argue that. You run that risk when you have too many value pop pillars. Of course, you need enough that allows you to stand out. If one or two are substantial, by no means add a third or fourth. If you find yourself adding extra value props, maybe because you were not as convinced about the first ones you had. They were never specific or unique enough.

So how do you find the right balance between having strategic and concrete value proposition pillars? You ask why and how.

When you are challenged as a B2B SaaS CMO or brand lead to making your value propositions specific, you need to use this methodology, aka the why/how ladder. Like any ladder outside the metaverse, the why/how the ladder is bidirectional. You either go up or down.


You step up the ladder to get to the why. Why is this important? Why does your customer/persona care? The answer to the “so what” question. So for each of the value propositions, you come up with, you need to ask “why” a couple of times to get to the real outcome that helps you create powerful messaging. 

For example:

You were conducting some positioning exercises, and you came up with a few value propositions that you think make you stand out. The first one is “Segment API compatible.”

You need to then go up the ladder, or ask something like “Why is this important?”

“Oh, our whole ICP uses Segment.”

“Why is that important?” 

“If they use us it’ll save them a ton of time doing XYZ.” 

“Why is that important? How much time does it actually save?”

Now the next answer after that is going to have a very specific ROI argument that you can make to make your value prop much stronger. That answer then should lead you to get more tangible results or outcomes that are driven by this superpower/value proposition. You end up with something like “Because now our customers can do XYZ. Save $xxx per hour…etc.

Until that is really a powerful argument, you keep asking why until you get to something that’s actually relevant for the actual customer.


You step down the ladder to validate that a value proposition is actually truly unique and to understand how it’s actually unique. What makes a specific feature an “only” for you? What’s your special approach that’s better than everyone else’s?

For example:

“Segment API compatibility is our superpower”

“How are we special in that? What do we do specifically that makes us special?”

“There are XYZ specific features that we offer that no one else has.”

You continue to go down the how ladder to verify if something is actually unique.

If you ever find yourself struggling with superpowers or positioning for your B2B SaaS, use the why/how ladder to find unique and specific value propositions. Both why and how at the end of the day help you in your messaging. The why part creates impactful messaging your audience cares about, and the down part/how part, gives you more credibility and makes your value props and superpowers more specific.