How to Run a B2B SaaS Positioning Workshop

How to Run a B2B SaaS Positioning Workshop

Sergio Iacobucci

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Protractor refracting rainbow light on black

Most startups jump straight to writing messaging (the words) without doing the work underneath (the thinking). That’s writing the ad before you know who you’re selling to. Or redoing the homepage for the 3rd time this year because it will solve all your problems. It’s tempting because execution feels like progress but unfortunately it’s not and it’s slower in the long run.

Here’s the flow:

Form the right team → Map what you’re competing with → Identify what you have that your competitor doesn’t → Validate that your customers and prospect actually care → Find the themes → Work out who cares most → Define the category → Write it down

1. Form the right team

Positioning is a business-wide exercise, not a marketing exercise. If only marketing is in the room, you’ll get a document that sales ignores.

You need, at least, these 5 people:

  • founder/CEO

  • product lead

  • sales/commercial lead

  • marketing representative

  • customer success lead

Small enough to make decisions. Big enough to avoid blind spots. This approach fosters buy in.

2. Map what you’re competing with

Notice how it doesn’t say WHO, that’s intentional and critical to this stage. Why? Because with competitors you need to include “do nothing.” 40% of lost deals go to the status quo. Meaning you list needs to include the status quo AND the shortlist of competitors. Map 3-5 real alternatives and be honest about whether you can dominate a segment or just participate.

Two main inputs:

  • Internal view: What does your team believe? Where do they disagree? That divergence is important data. When HomeServe asked 100 managers what business they were in, only 11 agreed.

  • Buyer view: What’s actually happening in your deals? Why do buyers chose you, why didn’t they, what alternatives did they consider? Most founders have never asked a lost deal why they walked away. And the CRM data is unreliable: salespeople get the full truth about win/loss reasons only 40% of the time (Anova). CRM systems tag the wrong competitor 65% of the time (Arkaro).

Within buyer research, look for three layers of urgency:

  • users - who want to do their job better

  • buyers - who have budgets and deadlines

  • external pressure - through regulation, customer demand, market shifts (that turns “nice to have” into “must have.”)

Word of caution - the evidence gap. Steps 2 (and 4) need buyer evidence most early-stage companies don’t have. Most founders have never asked a lost deal why they walked away. And what your team assumes about the buyer is likely to be more wrong than right. If you don’t have this evidence, everything that follows is built on guesses. If you haven’t had many deals, then fine. If you have, you need to do some win loss interviews.

3. Identify what you have, that your competition doesn’t

Don’t forget this includes vs the ‘do nothing’ status quo competitor in this evaluation.

Inventory everything.

Technical capabilities, yes. But also your customer success approach, onboarding, data infrastructure, domain expertise, pricing model, integrations, speed of iteration. Everything. Buyers take all of this into consideration. It’s tempting to only think about the moat created by your tech but that’s a software business mentality, the buyers care about the whole lot.

The list will be long. That’s fine. Filtering comes next.

4. Validate that your customers and prospects actually care

This is where most positioning exercises fall apart. Your team loves your features and your offering. The only ones that count for positioning are the ones customers call out and pay money for. Internal pipe dreams don’t qualify (repeat this in your head if you need to).

Two categories:

  • Core competencies: Important, without these your deals will fall over. Without them, deals will die. They are not unique, they are table stakes. You need them but you can’t differentiate on them.

  • Unique competencies: Specific to you AND valued enough by the market that buyers will pay for them. These need to come from evidence: buyer interviews, win/loss data, customer conversations. You’re looking for moments where someone says

“the reason we chose you over [alternative] was…”

No evidence yet? Get it before you finalise anything. Building positioning on assumptions is how you spend 8 years calling yourself “project management software” when your buyers use completely different words (the Basecamp story, via Bob Moesta).

49% of pricing power comes from positioning (Kantar). Getting this wrong costs you margin on every deal you win.

People are funny beasts sometimes. I’ve run into countless situations where their ‘perceived need’ during the sales process is weighted just as highly as the ones we know they’ll actually use. Be aware of this, don’t be blind and arrogant to it. If you need features to demo and sell, the product team should consider these seriously.

Word of caution - the evidence gap (again). This step is where the work from Step 2 pays off. If you skipped buyer research there, you’ll be guessing here too. No amount of internal brainstorming replaces hearing a customer say “the reason we chose you was…” Get the evidence before you finalise anything.

5. Find the themes within your competencies

Validated competencies start to cluster. Individual features group into bigger stories. This is good.

Speed of deployment + pre-built integrations + self-serve setup = “time to value.”

Compliance features + audit trail + data residency = “enterprise readiness.”

Buyers remember themes, not feature lists. Look at which clusters form naturally. If you’re forcing unrelated features into the same bucket, it won’t survive a real conversation.

6. Work out who cares about these the most

With the groundwork done, segmentation becomes clearer.

Which companies, industries, departments and people care most about your unique competencies?

Look at where you win and where you lose. Your best customers (buy fast, churn least, expand most, refer others) share characteristics. Those characteristics are your target market. Their firmographics will be what you’ll be able to build target lists from when it comes to refining your demand generation engine.

This will be narrower than you’re comfortable with. That’s the point.

Word of caution - the courage gap. This step means saying no to potential buyers. For a startup growing revenue, narrowing feels scary. But 53% of lost deals were winnable with a fixable misstep (Corporate Visions). Trying to be relevant to everyone multiplies those missteps.

7. Define the category and document it

What category are you in? Sometimes it exists and you take a position within it. Sometimes you need a modifier (“revenue intelligence” instead of “call recording,” as Gong did). Rarely should you create a new category from scratch.

Write down: who you’re for (specific enough for sales to qualify), the problem you solve (buyer’s language, not yours), unique competencies (validated), competitive alternatives and where you sit in the buyer’s mental map.

This document becomes the single source of truth for every conversation, every hire and every product decision. When it works, it feels like clarity.

Word of caution - the alignment gap. This document needs to be used, not filed. What usually happens: marketing builds positioning in a bubble, hands it to sales, sales throws it out. If the team from Step 1 doesn’t stay involved through activation, the positioning dies in a Google Doc.

Sergio Iacobucci, founder of Dialog

About Sergio.

About Sergio.

Sergio is a commercial marketing leader with a career defined by two major milestones: one exit and one IPO. He specialises in the B2B AI space, helping technical teams translate “what we built” into “why they buy”.

With 13+ years of experience from Customer Success through to CMO, he brings a disciplined, buyer-first lens to product marketing.

At Dialog, he cuts through the fluff to help startups crystallise their value and secure market share.