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From Marketing Spark · Nov 21, 2023

Brand Measurement: Why Positioning ROI Is So Hard to Prove

Every founder who has paid for positioning work eventually asks the same uncomfortable question. We rewrote the homepage, sharpened the story, retooled the messaging — so where's the line on the dashboard that proves it worked? The honest answer is that brand measurement is messier than anyone selling you a sprint will admit, and the founders who get the most out of the work understand that going in.

Every founder who has paid for positioning work eventually asks the same uncomfortable question. We rewrote the homepage, sharpened the story, retooled the messaging — so where's the line on the dashboard that proves it worked? The honest answer is that brand measurement is messier than anyone selling you a sprint will admit, and the founders who get the most out of the work understand that going in.

Drawn from Marketing Spark Episode 24 with Pedro Cortes, a SaaS messaging and conversion specialist.

The ROI question nobody wants to answer honestly

I had Pedro Cortes on the show because he and I share an obsession — turning muddled SaaS websites into pages that actually convert — and I wanted to push him on the part of the job most consultants tap-dance around. Pedro's tagline is that he helps SaaS companies turn more visitors into customers with better messaging and positioning. Mine is similar. So I asked the question I get asked every month by founders: how do you actually prove your work moved the number?

Pedro didn't dodge it. His short answer was that directly, you can't really correlate. Positioning sits inside a multilayered marketing mix — ads, content, outbound, events, referrals, podcast appearances that close a deal six months later. A founder will run a new homepage and an outbound push and a paid campaign all in the same quarter, then ask which one caused the lift. There's no clean way to isolate it unless everything else is dialed in and the messaging is the only variable moving.

That's the trap. Founders walk into brand measurement expecting attribution-grade certainty and walk out frustrated, because positioning doesn't behave like a Facebook ad. It compounds. It shows up in sales calls being shorter, demos converting faster, and prospects repeating your line back to you at a conference. Those signals are real, but they're not on a Looker dashboard at 9 a.m. Monday.

Why most B2B SaaS messaging is mediocre — and why nobody on the team notices

Before we get to measurement, it's worth being honest about why most SaaS websites need the work in the first place. Pedro pointed to two patterns, and I see both constantly with founders running $5M-$20M ARR companies.

One: they copy bigger companies. A Series-C-funded competitor can afford to be vague on the homepage because half the buyers already know the brand. You can't. When a $300M ARR competitor writes "the leading platform for modern teams," they get away with it. When you write the same thing, you're invisible.

Two: SaaS founders are product people. They geek out on features and capabilities and the engineering elegance of what they've built. Translating that into customer language is a different skill entirely — it's closer to charisma than to coding. So they write like robots, send the copy to the team, the team pats them on the back, and the website ends up reading like an internal pitch deck. Pedro called it the validation loop: founders write pages to make the leadership team feel smart, not to make the customer feel understood.

The result is the emperor has no clothes problem. Nobody inside the company points at the homepage and says it doesn't work, because everyone inside the company already knows what the product does. The buyer arriving cold doesn't, and they bounce in nine seconds. That's the gap a real messaging strategy closes.

The signals of bad positioning hiding in your sales calls

Pedro made a point that should be tattooed on every CRO's forearm: your demos are your highest-resolution diagnostic, and most teams ignore the data sitting in front of them.

If prospects show up to demos asking weird questions — basic stuff they should have understood from the website — your positioning is broken. If they arrive with the wrong expectation about what your product does, your positioning is broken. If they get to the demo and say "wait, you do that? I had no idea" — congratulations, your positioning is leaving money on the table. Every one of those reactions is a leak. The website is supposed to do the heavy lifting so the demo can close.

Pedro's framework for what a homepage must answer is brutally simple. Three pillars:

  • What result do you deliver? Not what features you ship. What changes in the customer's world.
  • Why are you better than what they're using right now? If they can't see a reason to switch, they won't, because switching software is painful.
  • How long does it take to set up? Most buyers assume implementation is a nightmare. If you don't kill that assumption explicitly, they'll kill the deal silently.

If those three answers aren't crystal clear above the fold, you have a positioning problem — regardless of what your conversion rate looks like. And the more skeptical the buyer (read: the bigger the deal), the more those three answers matter. Pedro pointed out that enterprise leads have tried more tools, are more skeptical of every claim, and are comparing you constantly in their head. They're the hardest to convert and they pay the most. They're also the ones who walk away silently when your messaging is muddled.

How Pedro actually measures positioning work (and why baseline beats attribution)

Here's where Pedro got practical. He uses two methods to measure brand and messaging work, and the choice depends on how much traffic the client has.

If there's enough traffic, he runs an A/B test. Straightforward — split the visitors, ship the new version, see what moves. The catch: most $5M-$20M B2B SaaS companies don't have homepage traffic that supports a statistically significant test in any reasonable timeframe. Marketing pages get a fraction of blog traffic, and the buyer's journey is too messy for a clean experiment.

When A/B testing isn't viable, Pedro uses what he calls a baseline test. The idea: before you change anything, document the current state. How many trials per month? How many demos? What's the average revenue per customer? What's the seasonality? If those numbers have been consistent for several months, you have a baseline. After the messaging change, the delta is your evidence. Not perfect — but defensible.

The most important thing Pedro said in the whole conversation, in my view, was this: he's biased toward revenue, not sign-ups. If a messaging change cuts sign-ups by 10% but lifts revenue per customer by 40% because the new copy filters out the wrong-fit buyers and pulls in better ones, he ships it. Every time. A lot of branding KPI conversations get hijacked by vanity metrics — bounce rate, time on page, scroll depth — that have no business driving a positioning decision. Pedro doesn't care if bounce rates go up. He cares if revenue goes up. That's the right hierarchy.

The KPI nobody puts on the invoice: confidence

I pushed Pedro on this and he agreed: there's a deliverable from positioning work that doesn't show up on any dashboard, and it might be the most valuable one. Confidence.

When a CRO walks into a sales call believing the story, the call goes differently. When a marketing lead can finally articulate what the company does in one sentence, internal alignment stops being a quarterly off-site. When the whole team is reading off the same page — same words, same proof points, same answer to the differentiation question — the company moves faster. That's not a metric. It's an outcome, and it's the one founders feel within weeks of finishing the work.

Directly, you can't really correlate. It's pretty hard. But a good entrepreneur knows that it takes time, and most good things give you indirect results. You're creating content on LinkedIn, you're doing podcasting, going to events — it took months and months to see actual results. You just had to trust the work. Even now you're not exactly sure how many clients came from podcasting, because you might have gotten a referral who watched your podcast and converted six months later, and they never told you. Positioning is the same. You build the conditions, and then you let the compounding happen.

Pedro Cortes

That's the honest answer. The founders who get the most out of positioning work are the ones who go in understanding that the ROI is part trackable, part directional, part qualitative. They use the baseline data they can get, they pay attention to the qualitative signals in sales calls, and they don't expect the messaging change to behave like a paid ad. For more on the underlying positioning work this measurement sits on top of, the framework I walked through with Clay Ostrom is the companion piece to this one.

What this means for your company this week

If you're running a $5M-$20M B2B SaaS company and you're trying to figure out whether your positioning is the bottleneck, do three things this week:

  • Document your baseline before you change anything. Trials per month, demos per month, demo-to-close rate, average contract value, and where leads are coming from. Three months of data is enough. Without a baseline, you can't measure anything later.
  • Listen to five recent sales calls. Count the moments where the prospect was surprised by what the product does. Count the times the rep had to re-explain what you sell. Every one of those is a homepage failure.
  • Pick the right north star and ignore the vanity metrics. Revenue per customer beats sign-up volume. Closed deals beat MQLs. If your messaging change moves the right number, you don't need a perfect attribution model to know it worked.

The companies that struggle with brand measurement aren't the ones with bad measurement tools. They're the ones who never wrote down where they started. Fix that first.

Ready to fix the positioning, not just measure it?

If your messaging is the bottleneck and you're a founder running a $5M-$20M B2B SaaS company, the Pipeline Story Sprint is built for exactly this — positioning, story, homepage, and the marketing plan that runs off them, in 90 days, fixed scope, fixed price. Not a fractional CMO retainer. If you want to talk through whether it's the right next step, reach out.

Listen to the full conversation
Breaking down the impact and ROI of B2B brand positioning and messaging

In the ever-evolving B2B SaaS landscape, clear messaging and strategic positioning are vital for standing out in the crowded marketplace.

In this episode of Marketing Spark, Mark Evans talks to Pedro Cortes about the intricacies of SaaS messaging, revealing why many companies struggle with branding and often end up with muddled messaging.

Cortes highlighted two main reasons for the widespread struggle with messaging among SaaS companies. 

First, many businesses tend to emulate the strategies of larger corporations, which can afford to be less clear due to their existing brand awareness. 

Second, SaaS founders are typically product people who geek out on the products and features they're building, often neglecting to translate their language into customer-centric messaging.

For anyone interested in my brand positioning and messaging workshop on Nov. 24, you can register here: https://lu.ma/6ugc7nu4