A syllabus. Read in order.

How I'm Doing AI as a CMO

These six pieces are how I'm thinking about AI transformation as a CMO, and the order to read them in. They're sequential by design. Each one assumes the one before it.

The premise underneath all of them: AI doesn't fix what's already cracked in a team. It accelerates whichever gaps you've got. Your people, your operating model, and the clarity you give the work are the moat. AI is the lever.

  1. Why Most AI Pilots Fail (And It's Not the Technology)
    01

    Why Most AI Pilots Fail (And It's Not the Technology)

    Start here. Most failed AI pilots aren't a tools problem. They're a clarity problem. Unclear customer, undefined roles, no shared definition of done. This piece is the diagnostic: the five questions to ask before you blame the model. Skip it and everything downstream stops looking like the same problem.

    Read the post →
  2. The People Work That Has to Come First
    02

    The People Work That Has to Come First

    Once you've named the gaps, this is how to close them. AI makes fast teams faster and misaligned teams misaligned faster. Read this for the four things only a leader can do, in the order they have to happen: define what good looks like, paint a vision worth moving toward, build the structure, calibrate the talent.

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  3. What Good Looks Like: How to Define Excellence for Your Marketing Team
    03

    What Good Looks Like: How to Define Excellence for Your Marketing Team

    Article 2 said to define what good looks like. This is how. Includes a worked example: the six First Principles I built with a 40-person B2B SaaS marketing team, and how WGLL shows up in hiring, calibration, performance reviews, and the hard conversations most leaders avoid.

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  4. What Your Team Actually Needs in 2026 (It's Not a Marketing Engineer)
    04

    What Your Team Actually Needs in 2026 (It's Not a Marketing Engineer)

    The high-level case for how marketing roles need to evolve. Hiring one “AI-native marketer” to sit at the centre of your team won't deliver what you think it will. Read this to see why the T-shape is still the model, and how craft experts paired with a marketing technologist outperform any single hybrid hire.

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  5. The New T-Shape: How Every Marketing Role Reshapes in an AI-Native Org
    05

    The New T-Shape: How Every Marketing Role Reshapes in an AI-Native Org

    Article 4 made the case for craft + technologist over a hybrid hire. This is how that idea becomes an org structure. The Mini CMO model in detail: one marketer owning an audience end-to-end, with Craft Custodians as strategic partners. Includes an interactive org chart showing how each CMO direct report transforms from legacy to AI-native, the time savings each transformation unlocks, and examples of the AI files that sit atop each workflow.

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  6. Map How Your Team Works Before You Automate Anything
    06

    Map How Your Team Works Before You Automate Anything

    You can't compress, hand off, or improve what you can't see. Process mapping is the unsexy infrastructure that turns one-off AI experiments into compounding gains. This is the workshop guide: what to look for, who should run it, and the baseline craft skill every marketer needs to develop.

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From the field.

The Craft

Operator-grade pieces on the leadership work that doesn't get written about. Hard calls, real failures, the conversations most leaders avoid.

When I failed as a leader.
The Craft

When I failed as a leader.

I kept a team member in the dark to protect the system. It backfired. This is the story I don't usually tell.

Yes. You should fire them.
The Craft

Yes. You should fire them.

You already know. The question isn't whether to do it. It's why you haven't yet.

Working Out Loud

Frameworks & Templates

GSD Process Map: B2B Marketing With and Without AI
Process Map

GSD Process Map: B2B Marketing With and Without AI

View framework →
Skills, Not Titles: How B2B Marketing Roles Are Evolving
Role Framework

Skills, Not Titles: How B2B Marketing Roles Are Evolving

View framework →
Process Mapping Toolkit

The workshop guide for mapping how your team actually works. Read the article →

Survey Template

Leader Diagnostic Survey

Open survey →
Survey Template

IC Diagnostic Survey

Open survey →
Process Map

GSD Campaign Launch Spreadsheet

Use template →
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Dear Swim Club Members only

The advice column for what you can't say at work.

Real questions from real people. The kind of stuff that isn't safe for LinkedIn and isn't easy to bring to your lead. Operator-grade answers. Completely anonymous.

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From Experiments to System

Three practical guides for CMOs and heads of marketing ready to move past disconnected AI experiments and build a system that actually scales — from framing the landscape to building your stack to leading the team.