I hear it from marketers in my DMs, WhatsApp messages, and emails, all wanting to know whether they’ll end up reporting to a sales leader in the future. I hear it a lot from my founder friends, mostly in SF, who’ve told me their plans to split marketing between product and sales because the version of a CMO they want isn’t findable. And the data backs this up. CMO roles in B2B are down by 10 percentage points over the past 12 months.

A growing number of founders now see marketing as two disciplines. There’s a growth discipline, and there’s a brand discipline. One marketing leader has continually failed to do both well. So the founder puts brand and product marketing into the product org, puts growth and demand into the sales org, and no longer has to worry about the marketing leader they’re constantly disappointed with.

Recently, Kipp and I did a full Marketing Against the Grain episode on this, coming out next week. It’s the number one topic we’re being asked about, so we did a deep dive. Be sure to subscribe to our channel to get the full breakdown. Here’s a summary of my takes.

Why it’s happening

Two things changed at the same time.

Founders changed. They used to ask their network, “Is my marketer any good?” and took months to work out the answer. I’ve been asked so many times to look over a marketing leader’s strategy and provide commentary for the founder: Is this good? Are they doing the right things? Now I’m finding a new batch of founders have real takes on marketing. They value the craft. They’re deep in the weeds. They have a clear sense of what they want, and they can tell quickly when they’re not getting it.

And the work changed. AI has pushed both halves of marketing to extremes. The growth side has to be more technical than ever. The brand side has to be better at narrative, creative, and positioning than ever. It is very hard for one person to spike at both, so the marketing leader ends up disappointing the founder on one of them.

Kipp named the paradox well on the show:

Marketing has never been more important, and that is exactly what’s killing the role. Expectations went up faster than the people did.

To give marketers some credit, every other C-suite role is complex but single-discipline. The CMO is the only one expected to understand positioning, brand, events, demand, and paid, and to be judged on all of them by a founder who has strong opinions on what all these things should look like and how they should impact their company.

The real failure is hiring

If you don’t have breadth across all of that, you need to excel at hiring. This is where I see most marketing leaders lose the founder’s trust.

If you don’t have core knowledge of a discipline, you can’t hire well for it. So you keep flailing in that role. And when the founder sits down with your VP of Brand and comes away unimpressed, they don’t think, “That VP is weak.” They think “my CMO is weak.”

Why the new structure doesn’t fix it

Here’s my problem with splitting marketing between product and sales. It doesn’t solve the problem. It just changes its shape.

Very few sales leaders know how to hire an incredible demand leader. Very few CPOs know how to hire a great product marketer. So instead of one person who’s not hiring the caliber of marketing you need, you now have two, and they don’t share the same quality bar. You’ve doubled the number of people making the exact mistake you were trying to avoid.

The structure also assumes growth and brand are disconnected. They aren’t. Your paid advertising at scale should align with your positioning, because when you stop spending, you don’t want to be forgettable. A demand team sitting in sales is thinking about feeding pipeline this month, not about what you want to be remembered for.

You would never split your sales team between product and marketing. It wouldn’t make sense. We wrote a whole book, Loop, on the idea that marketing is coming back to a team of generalists who can do far more with AI. To get the benefit of that change, the team needs to work as one unit.

Don’t lower the bar

The truest thing Kipp said on the show: doing nothing is better than doing the wrong thing. You are better off with no CMO than the wrong CMO.

The number one thing a bad marketing leader does is build a team in their image, and that takes years to undo. And the number one reason fast-growth companies hire mediocre marketers is that the bar drops under pressure to fill the seat. Every hire I’ve got wrong in my career traces back to that. I needed someone fast, so I convinced myself this was the person.

What I’d tell a founder

For the last 10 years, “can you help me hire my marketing leader?” has been the most common ask I get from founders. I’ve never had an easy answer. I’ve always found there was a limited number of people who fit exactly what they wanted. And they weren’t willing to compromise.

Here’s the best advice I had for them:

Find the person who spikes in both disciplines and sell them hard. They exist. They are just rare and usually locked up.

If you can’t, pick any structure that lets you hire good people without lowering your bar for the person who will eventually run marketing. Reporting into sales is, in most cases, going to be a disaster. Sales work on short cycles, and marketing needs, at times, to split focus between short-term and medium- to long-term wins.

Or take a bet. Hire someone you believe can be your head of marketing in 18 to 24 months, and pay a great CMO to advise them for a year. Most of what that person needs is to know what good looks like, how to manage senior people, and how to set up clear feedback loops.

And build a keep-warm list. Your dream hires are never available when you need them. I check in with mine anyway. Some of my best hires took 12 months of conversations before anyone was hiring or being hired. Kipp’s extension of this is the best advice on the show: put 3 to 5 of those people on light advisory, ask them questions, and you’ve just multiplied your odds that one of them joins when the timing finally works.

So is the role dying?

No. It’s in decline because the bar went up and the talent pipeline didn’t. We’re in a period of personnel-to-skillset mismatch. A new wave of marketers will come up who can do both halves of the job, and the role comes back with them.

If you’re a marketer, that’s the opportunity. The founders aren’t asking for less from marketing. They’re not actively looking to not hire a CMO. Their expectations of what that person can do are just different. But if you can meet them, there are plenty of opportunities.

Until Next Time,
Happy AI'fying,
Kieran

An explosion of sameness.

Wynter surveyed 100 B2B marketing leaders this year. 86% rated their own company as only “somewhat” or “slightly” distinctive. 6% said, “very distinctive.” It’s incredibly hard to sound different.

I’ve had so many conversations with founders and marketing leaders. They’re trapped in a positioning nightmare. What’s your positioning strategy when all products begin to look and sound the same? How do you position your product, deliberately defining why you’re different in a way that makes a specific market care?

This is one of the most critical parts of marketing today.

Perplexity didn’t try to out-search Google. They called themselves an “answer engine,” refused to show blue links, and never mentioned Google. $23B valuation in 30 months. Stripe repositioned payments to compete with PayPal by framing payments as a developer problem, made “7 lines of code” the entire pitch. They process over $1 trillion a year.

Positioning is HARD!

I’ve been quietly working on an entire marketing os. In this post, I want to share my positioning and web copy skills. It’s a mini system; it maps where you are, shows where you should be, and gives you the diagnostics to move.

Is it better than a world-class product marketer skilled at positioning and copy? No.

Is it better than what a lot of product marketers would produce? Is it incredibly helpful for teams and founders who don’t have a strong product marketer to work with? Yes.

→ Get the Positioning System on GitHub.

The Positioning Framework. What actually matters

Most of the marketing systems being pushed online have been created by Claude and Claude only. There isn’t anything unique about the skills within those systems when you dig in.

Some months ago, I found myself falling into the same trap. I built things with Claude but rarely checked its work. I rarely checked the context it was building for me, the skills, the plugins.

I’ve changed my approach to AI; I believe my domain expertise matters. I spend many, many hours working on a single skill.

The positioning skills are an example of that. I wanted to extrapolate what I felt truly matters for positioning. I wanted to map to some of the best advice from some of the best minds. But I didn’t just want it to be a dump of expert-led advice. I tested and iterated on what’s in that skill.

It features learnings from experts like April Dunford, Ries & Trout, Andy Raskin, Flint McGlaughlin, Anthony Pierri, Lenny Rachitsky, Emily Kramer, Elena Verna, Claire Suellentrop, and Bob Moesta. I distilled all that work into six principles:

1. Narrow your target ruthlessly. “Marketing teams” is millions of people. “Content marketers at B2B SaaS who publish weekly but can’t tell what’s working” is a target you can write for.

2. Start from the buyer’s reality, not your product. Lead with their problem, not your features.

3. Own one thing. Pick the single claim that matters most. Repeat it everywhere. Everything else is supporting evidence.

4. Differentiation must be concrete and defensible. Apply the competitor test: could your nearest competitor paste their name into this claim? If yes, it’s not a differentiator.

5. Positioning is cross-functional, not a marketing exercise. It shapes the homepage, the sales pitch, the pricing page, the ads.

6. Lead with a narrative about change. The shift in the world that makes your product urgent now.

I followed the same process for all my skills. The website copy skill I’m giving away comes from my experiences and learnings, paired with advice from some of the best copywriters throughout time. It includes things like using your customers’ actual words, not yours. Customers describe their problems better than any copywriter can.

These principles form the foundation of what I’m sharing in this post.

→ Get the Positioning System on GitHub.

1. Brand Context Template

Context matters so much more than skills. When building any AI system, no matter how large. Start by building a rich context set.

For positioning, we need to capture seven inputs: who uses it (jobs to be done), who buys it (if different), competitive alternatives (including “do nothing”), unique attributes that pass the competitor test, proof, and voice.

There’s also a key design choice that people don’t consider when doing positioning. For product-led growth companies, the user and the buyer are often different people. The person in the product daily and the person who approves the budget want to hear different things. You position for the user. But you need to layer in positioning for your buyer throughout certain parts of the buyer journey.

You can fill in this template in two ways. External AI research: scrape competitors, pull G2 reviews, search Reddit for how people describe the problem in their own words. Internal data: paste sales transcripts, support tickets, NPS verbatims.

For positioning, the single most important input is actual customer language. What they say, not what your team thinks they say.

Below is what’s included in the brand context template.

2. Positioning Skill

The positioning skill maps to the principles we talked about above.

It works against:

1. What’s changing in the world? (the urgency)

2. Who is this for? (narrow target)

3. What would they do without you? (the real alternatives, including doing nothing)

4. What do you have that they don’t? (with the competitor test applied to each claim)

5. Pick one thing. The hardest part. What’s the lead claim?

6. Choose your category. The frame that sets buyer expectations.

It supports two modes: first run (build positioning from scratch) and iteration (read your existing positioning, refine specific sections, show old vs. new delta). Another important tip when building AI systems is that the system should always feed learnings back into your context. In this case, you’ll keep updating your brand context after every product update, market shift, or competitor move.

The below is an example for the brand Wispr Flow. I recently fractured my elbow so have been using it a LOT. I used them as one of the brands to test my marketing os against.

→ The positioning skill and all six steps re in the repo. Grab it on GitHub.

3. Website Copy Skill

I’ve included one of my copy skills so you can translate positioning into website copy. The most common mistake i see people make when creating AI marketing systems is that they have one copy skill.

That just doesn’t work.

Website copy, creating a LinkedIn post, creating a YouTube transcript, creating a product launch video are all very different skills.

This skill is optimised to creating world-class website copy.

Five rules,

1. Use customers’ actual words, not yours.

2. Clarity before everything. If you have to choose between clever and clear, choose clear.

3. Lead with their problem, not your product.

4. Make every claim specific and provable. If you can’t prove it, cut it.

5. One page, one argument.

Here’s an example of what it did for WispFlow. The skill will create a HTML version of the home page. I think this is a great litmus test for positioning so you can review it.

→ The website copy skill includes the full expert-consensus ruleset. Get it on GitHub.

It will of course extract common AI patterns (what people call slop).

It’s a great bundle to have a co-worker help you iterate and brainstorm positioning for your company.

The full system

The full system is:

positioning-system/
├── context/
│ ├── brand-context.template.md ← Fill this in first
│ └── slop-patterns.md ← De-slop checklist for all copy output
├── product-marketing/
│ └── positioning.md ← Run this second
└── copy-team/
└── website/
└── website-copy.md ← Run this third

Each skill is written in conversational English, not written like an engineer.

I hope you enjoy.

Until Next Time,

Happy AI’fying

Kieran

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