How to Run a Positioning Workshop: The PMM's Step-by-Step Playbook

Every B2B SaaS company has a positioning problem. The VP of Sales describes the product one way. The CEO pitches it another way at conferences. The website copy was written two years ago by someone who no longer works there. Marketing is generating leads for segments the product team isn't building for.

The symptom shows up in the data: win rates that plateau, messaging that doesn't resonate, sales reps who wing their pitches because nothing they've been given actually lands.

The usual response: a new brand refresh. New messaging copy. A new campaign. None of it addresses the actual problem, which is that the organization has never aligned on what makes them genuinely different, who they're genuinely best for, and what they need to stop saying.

A positioning workshop, done well, fixes that. Not permanently — positioning is a living thing — but it creates shared language, a documented stake in the ground, and a foundation every team can build from.

This is the playbook for running one that actually sticks.

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Why Most Positioning Workshops Fail

Before the framework, the failure modes. Most positioning workshops go wrong in one of three ways.

They generate enthusiasm, not alignment. Two hours on sticky notes, someone synthesizes the output into a slide, everyone nods, the slide goes into a shared folder, and nothing changes. The problem is that sticky-note brainstorms surface opinions, not market reality. The output reflects what people in the room believe, not what buyers actually respond to.

They're run by the wrong person in the wrong way. Positioning workshops facilitated by people with a stake in the outcome are compromise machines. The CMO wants the premium narrative. Sales wants simpler. Product wants the technical differentiation front and center. The facilitator mediates rather than diagnoses, and the result is a consensus document that doesn't make anyone particularly wrong and doesn't make the company particularly differentiated.

They skip the pre-work. A positioning workshop is not a brainstorm. It's a structured synthesis of what you already know about your market, your customers, and your competitors. Teams that skip the pre-work spend the workshop arguing about facts that should have been established before anyone walked in the room.

The fix for all three: treat the workshop as a diagnostic, not a creative exercise, anchor everything in external evidence, and do the research before the session starts.

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What You're Actually Doing in a Positioning Workshop

A positioning workshop has one job: get organizational alignment on a positioning statement that is true, differentiated, and resonant.

True means it's grounded in what you can actually deliver and prove. Not aspirational. Not "we want to be the leader in X." What's actually true about your product and company today.

Differentiated means it's not a claim every competitor could make equally. "We're fast, easy to use, and have great support" is not differentiation. It's table stakes. Differentiation is the specific claim only you can make, backed by specific proof.

Resonant means your buyers actually care. The most elegant positioning in the world is useless if it's aligned around a value that doesn't map to what buyers are trying to achieve.

The workshop surfaces these three dimensions by bringing together people from different parts of the organization — product, sales, marketing, customer success, executive team — who each hold different pieces of the puzzle. The PMM's job is to structure the conversation so those pieces come together into something coherent.

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The Five-Phase Framework

Phase 1: Pre-Work (1–2 Weeks Before the Workshop)

The workshop session itself should be a synthesis and alignment exercise. The raw material — market data, customer language, competitive intel — needs to be gathered and organized before anyone enters the room.

Stakeholder interviews (45–60 minutes each):

Interview 6–8 people across functions: 2 AEs, 1 SDR, 1 CSM, 1 product manager, 1 executive (CEO or CMO), and 1–2 customers if possible.

The questions that matter:

• "If you had to describe what we do in one sentence to someone who's never heard of us, what would you say?"
• "Who is our best customer? What do they have in common?"
• "Why do we win? When a deal goes our way, what was the deciding factor?"
• "Why do we lose? What's the real reason, not the diplomatic answer?"
• "What do competitors say about us? What do we say about them?"
• "What's the one thing we should stop saying about our product?"
• "What do customers say when they recommend us to someone else?"

Write down the exact language people use. Don't paraphrase. The verbatim quotes from stakeholders — especially from customers — become the raw material for the workshop.

Competitive audit:

Map the 3–5 primary competitors on two axes: what they claim their product does and who they say it's for. Use their own words from their websites, landing pages, and sales decks. This becomes the backdrop against which your positioning needs to differentiate.

Look for the whitespace: claims no one else is making, segments no one else is targeting, proof points no one else is using.

Win/loss review:

Pull the last 10–15 won and lost deals. For won deals: what triggered the purchase? What was the deciding factor cited in CRM notes or customer conversations? For lost deals: what was the real reason — not "budget" or "timing" — behind the decision?

If you don't have this data, that's a finding in itself. But work with what you have.

Pre-read document:

Synthesize all of this into a 3–4 page pre-read document you send participants 48 hours before the workshop. It should include: current positioning (whatever exists today, warts and all), a summary of what you heard in stakeholder interviews, competitive landscape overview, and 3–5 key tensions or questions the workshop needs to resolve.

Sending a pre-read accomplishes two things. It ensures everyone walks in with shared context. And it signals that this is a serious exercise, not a team-building activity.

Phase 2: Market Anchoring (45 minutes)

Start the workshop session by establishing shared facts about the market. This is not discussion time. It's orientation time.

The opening sequence:

1. State the purpose and ground rules (30 seconds). "We're here to align on positioning — not brainstorm, not rebrand. We're going to work through structured exercises. Please hold opinions until we've looked at the evidence."

2. Walk through the competitive map you built in pre-work. Show where each competitor positions, using their own language. Ask the group: where are we on this map today? Where do buyers put us?

3. Surface the key tensions from your stakeholder interviews — without attribution. "In our pre-work interviews, we heard X from people in sales and Y from people in product. We need to resolve that today."

4. Share the most instructive customer quotes from win/loss data. Let buyers' language anchor the room.

The anchor question: "Based on all of this, where is the real whitespace in this market — the position no one else currently owns that we could credibly claim?"

Write responses on a whiteboard or shared doc. Don't evaluate them yet. Just surface them.

Phase 3: Differentiation Mapping (60 minutes)

This is the core of the workshop. You're building two things: a list of candidate differentiation claims and a ranking of those claims by what's actually true and what buyers actually care about.

Step 1: Generate differentiation candidates (15 minutes)

Ask participants to write down — individually, before discussing — their answers to: "What can we say that our competitors genuinely cannot say? What do we have that no one else has?"

Give them 5 minutes of individual thinking time. Then collect the answers. Group them by theme. You'll typically see 4–6 clusters: product capabilities, customer outcomes, business model, team or domain expertise, data or network effects, speed or implementation approach.

Step 2: Apply the differentiation filter (20 minutes)

For each candidate claim, run it through three questions:

• Is it true? Can you prove it with evidence — a feature set, a case study, a metric, a customer quote? If you can't prove it, it's aspiration, not positioning.
• Is it different? Would competitors say the same thing? Pull up their websites. If three competitors make the same claim in similar language, it's a table-stakes claim, not a differentiator.
• Does it matter? Did buyers say this was a reason they chose you? Did it come up in win/loss data as a deciding factor? If the claim doesn't map to buyer decisions, it's irrelevant no matter how true it is.

Claims that pass all three filters go to the top of the list. Claims that pass only one or two are noted but deprioritized.

Step 3: Rank and sequence (25 minutes)

Take the claims that passed the filter. Rank them: which one is the most important thing you can say? What comes second and third?

This is where workshops get contentious, because different functions have different priorities. Sales wants the message that helps them close deals fastest. Product wants the capabilities that took the longest to build. Marketing wants the story that's most interesting to write.

The PMM's job as facilitator: bring it back to buyer evidence. "Which of these did buyers cite most consistently in win data? Which resonates when sales uses it in discovery?" The answer to that question ranks the claims, not anyone's internal conviction.

By the end of this phase, you should have: a primary differentiation claim, 2–3 supporting claims, and a clear sense of what your positioning is not going to be built on.

Phase 4: Draft Synthesis (30 minutes)

With differentiation claims ranked, you're ready to draft a positioning statement. This is not a marketing tagline. It's an internal document — the formal statement the organization uses to make downstream decisions.

The classic positioning statement format:

For [target customer], [company name] is the [category or reference frame] that [primary differentiation claim], unlike [alternatives], because [proof points].

Work through it live in the room. Don't try to get it perfect. Get it to "good enough to debate."

A working example for a sales intelligence platform:

For enterprise sales leaders managing complex, multi-stakeholder deals, Meridian is the revenue intelligence platform that surfaces buying committee risk before it becomes pipeline risk, unlike CRM-native tools that track activity without predicting outcomes, because our AI is trained on 50 million enterprise deals across 12 industries.

Walk through each element:

• Who is the specific target customer? (Not "everyone." The ICP — the buyer who gets the most value, fastest.)
• What is the category framing? (Where does the buyer's mind already go? You're either owning an existing category or explicitly creating a new one.)
• What is the primary differentiation claim? (The one claim from the ranked list that goes first.)
• What are the alternatives? (Not competitors by name — the approach buyers would take without you, including "doing nothing" or "using spreadsheets".)
• What is the proof? (The supporting evidence that makes the claim credible.)

Draft it, put it on the screen, and critique it as a group. Expect three or four revisions before you have something the room can live with.

Phase 5: Pressure Testing (30 minutes)

The worst thing that can happen after a positioning workshop is that the output sounds good in the room and falls apart the first time someone uses it.

Pressure test the positioning statement with three simulations.

The sales call test:

Ask an AE in the room to play a prospect. Run the opening of a discovery call using the new positioning as the frame. Does it flow naturally? Does the "prospect" understand the problem being solved within the first 30 seconds? Does the differentiation claim mean anything to someone hearing it for the first time?

This simulation consistently reveals language that's too internal or too technical. Fix it before you leave the room.

The competitor test:

Pull up a competitor's homepage. Ask the group: if a buyer had just visited this page and then came to ours, would the distinction be immediately clear? Does our positioning create distance from theirs? Or do they overlap?

If the positioning blurs with a competitor's, you haven't differentiated enough. Go back and sharpen the primary claim.

The proof test:

For every claim in the positioning statement, someone in the room has to name a specific piece of evidence. A case study. A metric. A customer quote. A feature set. If a claim can't be proven in the room, it shouldn't be in the positioning.

If you reach the end of Phase 5 with a positioning statement that passes all three tests, you have a working foundation.

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After the Workshop: Making It Stick

A positioning workshop that produces a document and nothing else hasn't changed anything. The real work is operationalizing the output.

Document it formally. Create a positioning brief: the statement, the differentiation claims in ranked order, the ICP definition, the primary proof points for each claim, and the list of claims you explicitly chose not to lead with. Put it somewhere permanent and accessible — not in a shared meeting doc that gets buried.

Brief every customer-facing team separately. Don't send the document and assume adoption. Run 30-minute briefing sessions with sales, SDRs, CSMs, and marketing. Show them how the positioning connects to their daily work. Show sales how to use it in discovery. Show marketing how it should shape content. Show CSMs how to use it in expansion conversations.

Update the ICP and messaging frameworks immediately. The positioning statement informs these, not the other way around. Once positioning is set, revisit your ICP description, your messaging house, and any active sales decks or campaign copy.

Set a review date. Positioning isn't permanent. Markets change. Products evolve. Competitive landscapes shift. Schedule a positioning review 6 months out to evaluate whether the claims still hold and whether the market is responding to them.

Track whether it's working. The signal that positioning is working: sales reps are using the language without being prompted. Prospects are using the language back to you. The deal questions you're getting are getting better (more specific, more aligned with the problems you solve). Win rates in your primary ICP segment are improving.

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Facilitation Tips for PMMs

Running a positioning workshop is as much a facilitation skill as it is a marketing skill. A few practical notes on making it work.

Control the agenda visibly. Use a shared doc or whiteboard that everyone can see. Write the agenda at the top. Move through it deliberately. Workshops go sideways when the facilitator allows one tangent to eat the session.

Separate data from opinions. When participants are debating, ask "is this a claim we're making or evidence we have?" The data phase and the opinion phase should be distinct. Evidence first. Synthesis second.

Protect the ICP conversation. The instinct of almost every team is to want to sell to everyone. Part of the workshop's value is getting organizational buy-in on the truth: you can't position for everyone, and trying to do so positions you for no one. Be direct about this.

Use silence. Give participants time to write before they speak. Individual thinking before group discussion produces better answers and prevents the most vocal person from anchoring the group.

Don't take a position until Phase 4. Your job in Phases 1–3 is to surface and organize, not to argue for a particular direction. Save your POV for the synthesis phase, and deliver it as a synthesis of what you heard, not as your personal take.

Handle the CEO. If the CEO is in the room, their opinion will anchor the group unless you actively manage it. Thank them for their input. Then return to buyer evidence. "You're right that we believe this — does the win/loss data support it?" This isn't political. It's methodological. Position it that way.

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A Note on Remote Workshops

Everything in this framework works in a remote setting. A few adjustments.

Use a collaborative whiteboard tool (Miro, FigJam, MURAL) for the visual exercises. Set it up before the session and share the link with instructions. Don't figure it out in real time.

Send a detailed pre-read with 72 hours lead time instead of 48. Remote participants need more context to engage well with a session they're attending via video.

Run the session in two 90-minute blocks with a break between Phases 2/3 and Phases 4/5. Four unbroken hours on video is too much. The break also gives people time to process before the synthesis and pressure testing.

Use private notes (DMs) instead of individual thinking time where possible. Remote participants won't write independently if they can see the chat. Ask them to DM you their responses before revealing them to the group.

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