Why Positioning Is So Dang Hard for B2B SaaS

 

Hi, I’m Ben Watkins 👋 Thanks for joining another edition of La Vie Ben Rose. Every week, I unravel messaging and positioning systems around B2B, so you can grow faster and smarter (and earn more green).

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B2B Positioning Playbook

Back in the day, I was a middle school teacher, and I had this trick for getting two students to tell me the truth.

I pull one of them aside and say, “Your friend told me the truth. Let’s see if your story lines up.” Then they’d usually tell me the truth, and they didn’t collaborate with each other on making up some wild tale.

Positioning is the opposite of that.

You want to get everyone in the same room, figure out the customer journey / story, understand what existing customers love about you, and where they would go if you didn’t exist (Thanos snap edition).

The Positioning Fog (Healthcare SaaS Style)

Positioning is context. That means you frame your product so your buyers instantly recognize what you do and how you do it.

Here are some examples

  • Confused buyers → They can’t tell how you’re different, so they default to the safe choice (not great for you).
  • Longer sales cycles → Every call becomes a re-education.
  • Weaker demos → You’re explaining what it is instead of why it matters.
  • Misfired marketing → Campaigns chase buzzwords instead of clarity.

Here’s how the fiery fog of doom comes about

And it rarely comes from incompetence. It’s actually disguised as success in silos.

  • Founders talk in investor language: markets, TAM, and tech.
  • Sales speak in prospect pain.
  • Marketing pushes feature headlines to “sound strategic.”
  • Product lists capabilities to prove maturity.

They never work together to show the unified customer journey. They never work together to find that value differentiator that matters the most to the audience.

How to get rid of the fog

When I start working with a health tech company, I help them align on positioning.

It’s not a blockbuster Marvel movie excitement. But it’s necessary to get rid of this positioning fog.

Here’s what we look for:

  1. Stakeholder Interviews – I ask 5–10 internal leaders, “What problem do we solve, and for who?” Then I map the deltas.
  2. ICP Mapping – Not just titles, but emotional jobs-to-be-done. What do they fear, fight, and dream of fixing?
  3. Voice of Customer (VOC) – I pull transcripts from sales calls and demos to capture the language buyers actually use.
  4. Competitive Frame Check – What category are you unconsciously competing in AND is it the one that puts your strengths at the center?

By the end, I can usually summarize the company’s fog in one sentence:

“You’re saying what you do. Your buyers need to hear why it matters.”

How to Align Your Positioning

Here’s the simple (but not easy) way to clear your positioning fog:

  1. Name Your Real Competitors (Not the Ones You Made Up)
    Not the ones on your pitch deck. The ones your buyers would use if you didn’t exist: spreadsheets, manual workflows, status quo. The ones they actually talk about.
  2. Map Attributes to Value
    Features don’t sell. Translating those into customer value themes does. Boom.
  3. Find the Frame of Reference That Flatters You
    You’re not a “platform.” You’re a “clinical decision partner” or an “outcomes automation engine.” Choose a frame where your strengths look obvious.
  4. Align the Whole Team
    If marketing’s saying one thing and sales another, it’s not alignment — it’s noise. Capture your positioning so everyone can use it.

Above all, remember that you can’t out-market misalignment. You can’t out-email it, out-demo it, or out-pivot it. You can’t out-work bad positioning.

You have to ask the central question that matters:

“If I weren’t here to explain it, would our buyers still understand what we do and why it matters?