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How to stop guessing what to say to your ICPs

I ran a roundtable yesterday with a group of founders, PMMs, and early-stage marketers. We were talking about messaging and positioning, and within about ten minutes, three different conversations coalesced into the same problem.

One person had just raised a big round. Their product had evolved significantly, but messaging hadn’t kept up. They described the internal process as “executive therapy” (messaging is therapy when done well!) everyone had a different version of the story, and nobody could agree on which one to tell.

Another had been in their role two weeks and had a clean slate and their CEO was asking for messaging pillars on day one. They’d taken screenshots from my session because they didn’t know where to start.

A third was working around a founder who hard-coded the website six years ago and wouldn’t let anyone touch it. So the landing pages said one thing, the website said something else, and the sales team was improvising somewhere in between. “The message that works is not the message on our website,” they said. “And that’s the problem.”

Three different situations. Same root cause: no system. No shared foundation to return to when things stopped working.

Last week, I wrote about how your website is becoming a sales conversation — and how you can’t have that conversation without documenting your value proposition in layers. I introduced five layers, from your positioning anchor down to ICP playbooks.

Today I want to go deeper into what those layers actually look like, especially the last one, because that’s where strategy finally becomes something your team can use.

The architecture (a quick recap)

The system has three main components. Think of it less like a document and more like an operating system for your messaging.

The Core Messaging Framework is your north star — your market category, strategic narrative, core value proposition, and the three to four universal pillars that run through every communication regardless of audience. This is the layer that defines what you stand for. It doesn’t change based on who you’re talking to.

The Value Proposition Canvas sits behind the scenes as the thinking layer. For each ICP, you map their specific pains, jobs-to-be-done, desired outcomes, and objections against your universal pillars. You’re not creating new strategy here but instead you’re figuring out which part of your existing strategy leads with each persona, and what language will actually resonate.

The ICP Playbooks are where it all becomes executable, which is where most teams either stop short or get it wrong.

What does an ICP Playbook actually look like?

A playbook is the day-to-day tool, what you pick up before a sales call, when briefing a campaign, writing a cold sequence, or onboarding a new hire who needs to understand who they’re talking to.

Here’s what a complete playbook includes:

1. Persona Overview

Not a demographic profile. A real picture of who this person is, what they’re accountable for, and how they think/make decisions. The pain points that keep them up at night. The motivations underneath the job title. The functional, emotional and social jobs to be done.

2. Market Category (Reframed for Them)

Same product, different lens. How does your category land differently depending on who’s evaluating it? A CMO and a Head of Growth are often buying the same thing for different reasons, using different mental frames. The playbook makes that explicit.

3. ICP-Specific Value Proposition

This one is adapted from your core value prop. It simply translates it into their world — their language, their priorities, their version of success.

4. Messaging Pillars Translated into Benefits

The playbook takes each pillar from the core messaging framework and expresses it specifically for this persona. We take the same theme, and write it down as seen from a different lense (pain, gain, benefit, logical, and short description)

5. Sales Pitch Variations

Here we a write a short 60-second version of the pitch for a quick intro, a two-minute version for a proper conversation and another quick version for outreach. Each one starts from where this persona is (the conversation they’re having in their heads!), not from where you want to take them.

6. Objection Handling

These are the specific hesitations this persona brings to the table, and our honest, direct responses to each one. This section alone is worth building the playbook for, because objections are where most conversations break down.

7. Proof Points Tailored to Them

This is one of the most underrated sections. A Head of Growth and a PE Operating Partner care about completely different evidence. Generic stats don’t move either of them. Proof points need to match the persona’s priorities, meaning what they’re measured on, what they report to their board, what makes them look smart or exposed.

8. Channel and Context Adaptations

How does your messaging change when you move from a cold email to a LinkedIn post to a live demo? Tone, emphasis, structure, length — all of it. The playbook spells this out so your team isn’t guessing every time they switch channels.

9. Example Copy Blocks

These are just useful starting points. Headlines, email openers, social snippets — written in the persona’s register, for the contexts they actually appear in. The goal is to give your team something concrete to work from instead of the dreaded blank page.

The key idea behind all of it

You shouldn’t change your strategic narrative because you’re talking to a different persona. And you shouldn’t rewrite your value proposition for every audience.

What makes this a system and what should change is which pillar leads, what language you use, what proof you reach for, and what emotional tone opens the conversation.

The playbook answers those questions so your team doesn’t have to improvise them in real time.

And that’s what prevents the two failure modes I see most often.

The first is saying the same thing to everyone and connecting with no one. The second is over-customizing — every rep and every marketer off-script, inventing their own version of the story until nobody’s quite sure what the company actually stands for anymore.

In practice:

• always start with the Core Messaging Framework to make sure you’re aligned
• use the VPC to understand what actually matters to the persona you’re writing for
• pull the most relevant insights into the playbook

And when you learn something new from the field, update the VPC first, then the playbooks follow. The core stays the same unless something fundamental changes about who you are and what you stand for (positioning).

The people in that roundtable were struggling because they were trying to write their way out of a structural problem (or, better, their organizations forced them to)

Copy isn’t the answer when the foundation isn’t there. The answer is building the system first, and then letting the copy flow from it.

That’s what a messaging operating system actually is.

Building this for your own company or clients? Reply and let me know where you’re stuck. Happy to think through it with you.

DISCOVERY

New episode of The Message-Market Fit podcast 🎉

​This week on the podcast, I sat down with Sam Woods — a machine learning pioneer turned Fractional Chief AI Officer — to talk about what actually wins in an AI-saturated world.

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We explore:

• Why the flood of “AI slop” makes strong ideas more valuable than ever
• The real bottleneck behind low conversions (hint: it’s not your copy)
• How to think in systems instead of isolated landing pages
• When to automate with AI — and when to keep a human in the loop
• What the future of copywriters really looks like (and who will thrive)

If you care about message–market fit in the age of AI, you’ll want to hear this one.

How to use live events as key growth lever in 2026

My friend Maja published a super useful newsletter on live events in B2B. As I’m personally doing more of these this year, I’m really interested in learning how to plan and strategize around them. With the mountain of AI slop going around online these can be your secret weapoin, especially if you have a strong POV, lots to teach, and a great product to promote.

Get clarity on what AI tools you should use

Ethan Mollick released his updated guide to AI tools and models. If you feel overwhelmed and in a rush to try everything under the sun, this might help at least give you a very good overview of what’s happening and what tools could help you get more bang for your buck.

RESONANCE

Richard Shotton, The Choice Factory

Have a great weekend!

Cheers,

Chris

Chris Silvestri Founder & conversion alchemist

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