Positioning Is Not a Messaging Exercise. It’s an alignment exercise.
The CTO looked at me, slightly frustrated.
“Why do we always get stuck here?”
We were deep in a positioning workshop at a Series B AI procurement startup I had joined in 2023.
Whiteboard full.
Coffee cold.
Half the room debating differentiators.
The other half debating the benefits of our product.
It wasn’t the first time we’d had this conversation.
And that was the point.
When I joined, the mission sounded simple: help procurement teams find suppliers faster.
In practice, the company felt split into parallel realities.
Sales were pitching what they personally believed resonated. No two decks were quite the same.
Marketing was running demand generation with confident but generic messaging.
The website spoke about transformation and intelligence, yet it wasn’t clear what the product concretely did.
At the same time, Product — including the founder — was energised by a new idea. A concept inspired by a couple of prospective customers. It wasn’t built yet. But there was pressure to sell it.
Meanwhile, the only tangible product available was the company’s core supplier discovery platform.
So Sales sold what existed.
Marketing partly spoke about what existed and partly about what might exist.
Product focused on what was coming next.
Everyone was moving fast.
Just not in the same direction.
The customer base reflected that ambiguity.
There were around a few loyal enterprise and mid-sized customers — mostly manufacturers — paying significant contracts to help them find specialised suppliers.
There were a few hundreds occasional users operating on a pay-per-search model. Many didn’t use all their credits. Some never renewed.
And in the CRM sat thousands of leads collected from seven years of trade shows across Europe and the US. Badge scans. No filtering. No clear Ideal Customer Profile.
At first glance, it looked like a pipeline problem.
But when you listen closely to sales conversations, you hear something else.
Prospects were unsure how we were different from other supplier databases.
Internal teams disagreed on who our real competitors were.
Benefits shifted depending on who was speaking.
It wasn’t a demand issue.
It was a clarity issue.
Two weeks before I joined, a new Head of Product had started. She brought strong experience in product discovery and product-market fit methodology. While she focused on validating the new conceptual product, I focused on the existing revenue-generating platform.
Around the same time, the product was being redesigned to include generative AI capabilities.
And a new objection started appearing in sales calls:
“Why would I pay for this when I can just use ChatGPT?”
OpenAI’s ChatGPT had changed the reference point.
If supplier discovery could be done through a prompt, what exactly was our advantage?
That was the moment I proposed running a positioning workshop, using the canvas popularised in Obviously Awesome by April Dunford.
It was the first time positioning had been approached structurally in that company.
I tried to make it easy for everyone.
Two sessions.
Morning or afternoon.
Join when it suited them.
In the session where the CEO dialled in, discussions were smoother. We moved quickly through market category, competitors, product attributes. Consensus came relatively easily.
In the second session — without the CEO but with Product, Tech and Strategy leaders — it was different.
We stalled.
On ICP.
On differentiators.
On benefits.
We debated for hours. We couldn’t finish in one sitting.
At the time, it felt inefficient.
Looking back, it was healthier.
The first group carried years of history about what the product “had always been.”
The second group — newer leaders — questioned more. They were less attached to the past.
I collected all perspectives and synthesised a unified positioning.
On paper, it worked.
In reality, it felt clunky.
No clear focus on a shortlist of competitors.
Differentiation that tried to satisfy everyone.
Benefits that sounded cautious rather than compelling.
I had accommodated availability.
But I hadn’t created alignment.
And positioning without alignment is fragile.
A couple of months later, when the redesigned AI-enhanced version was getting ready to be launched, I ran the workshop again.
This time there were no split sessions.
One room.
All core GTM and technical leaders present together.
Attendance was strong. Focus noticeably higher. Laptops mostly closed.
Something had shifted. The first workshop had made the cost of misalignment visible. People were aware of the problems we had and were paying more attention.
We worked through the canvas again.
And again, we got stuck on differentiators and benefits.
That’s when the CTO asked, “Why do we always get stuck here?”
Because that’s where trade-offs live.
You can’t position against twelve alternatives.
You can’t claim fifteen strengths.
You can’t serve everyone equally well.
Positioning forces you to choose.
In a startup conditioned to run at speed, slowing down to choose feels uncomfortable.
But speed without clarity is expensive.
This second workshop felt tighter. More focused. More honest.
For the first time, Sales, Marketing and Product described the product in the same way.
Not perfectly.
But consistently.
That consistency reduced friction in sales conversations.
Marketing became more targeted.
Internal meetings became less defensive.
Positioning didn’t magically fix everything overnight.
But it created alignment.
And alignment changes trajectories.
There’s a narrative emerging that in the age of AI, great products sell themselves.
It’s true that product development has accelerated. Features that once took months can now be prototyped in days.
But something fundamental hasn’t changed.
The number of software options available to buyers has increased dramatically.
Human cognitive capacity has not.
When everything feels possible, clarity becomes more valuable — not less.
AI lowers the barrier to building.
It does not remove the need to decide:
Who is this truly for?
What problem does it solve better than the alternatives?
Why should someone choose this over the two or three options they’re realistically considering?
Speed without clarity simply produces more noise.
What I took away from this
Positioning must be done synchronously with the right people in the room. Alignment cannot be stitched together afterwards.
Before defining differentiators, teams often need to let go of historical identity. Alignment is emotional before it becomes tactical.
Clear positioning reduces wasted acquisition effort. The sharper the ICP and differentiation, the lower the friction in buying conversations.
You may take something different from this.
I’d genuinely be curious what stood out to you.
If this tension feels familiar in your organisation, you’re not alone.
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And if you’re navigating something similar in your organisation, you’re welcome to reach out. I’m always happy to have a thoughtful conversation.