Revenue Diaries Entry 24

Inside: Ignore the News, Two Ideas for New AI Org Structures, and Interviewing Go-To-Market Jesus

Every four years, America goes into election mode.

Cable news gets louder. Social feeds get angrier. And suddenly, even marketers start sounding like pundits.

A few days ago, the admirable Dr. Julie Gurner posted on LinkedIn commentary that now lives in my head rent-free (with the thousands of other quotes from Julie I’ve read over the years).

“To win big at anything, you have to be hard to kill.”

That line has been bouncing around my head ever since.

Because she’s right. Especially in a year like this.

I get it. I really do. What happens in politics feels like it affects everything. And to some degree, it does. But I’ve made a personal rule: I don’t write about politics. Not in my newsletter. Not on LinkedIn. Not in decks.

Why?

Because I believe the moment you start giving external forces that much power over your mindset, you’ve already lost.

Naval Ravikant once said: “The news is the mind’s junk food. Ignore it and build.”

That line has joined the thousands of quotes from Dr. Gurner and has been burned into my brain for years. It reminds me that outrage is easy. But discipline? Focus? The ability to keep building in the middle of chaos?

That’s the real work.

And that’s what I admire most in the people I’ve worked with over the years… especially in marketing: the ones who don’t just ride momentum but create it. The ones who keep shipping when the market crashes, when the budget vanishes, and when leadership changes.

The best marketers I know? They’re hard to kill.

Not because they don’t care what’s happening in the world. But because they don’t let it knock them off their game. They’ve trained themselves to focus on what they can control. Their attitude. Their output. Their people.

They stay steady when others spiral.

So yeah, vote. Care. Rally. Speak up when it matters.
But if you’re leading a team, growing a business, or trying to make something real?

Don’t get distracted. Don’t get dragged into someone else’s algorithm.

Stay hard to kill.

❤️ kyle

Thanks to Share Your Genius, who is our first partner in the newsletter and podcast. I’ve known the team and their CEO for years. They are the best creative agency, helping brands build deeper relationships with their audience through binge-worthy podcasts and great content.

On Go-to-Market Jesus, Shiny Objects, and AI That’s Doesn’t Suck

I don’t usually talk work on the podcast.

In fact, the whole point of Revenue Diaries is to talk about anything but work.

But for episode 8, I broke the format. Why?

Because I’ve been watching Jordan Crawford for a while. And he’s one of the few people who can actually talk about AI, go-to-market, and sales development in a way that’s not completely insufferable.

So we went deep… on AI, on Clay, on why the outbound model is broken, and on how to actually fix it.

A few highlights worth your time:

“Your knowledge should compound, not fracture.”
This is Jordan’s test for whether your GTM motion is working… especially in horizontal SaaS. If you’re learning about your customers and getting less clear over time, you’ve got a problem. Instead, pick the segment where your knowledge compounds and go all-in.

From donut shops to buffets to broken glassware
Jordan uses food metaphors like a wizard. The point? The old world of outbound (ZoomInfo, Apollo, intent data) was like a donut shop — easy, with limited options. The new world (Clay, AI, microagents) is a Bellagio buffet — overwhelming unless you’re intentional. Most teams are just loading up their plate and hoping for the best. Don't be most teams.

Start with real customer insight. Then scale.
The Overjet example blew my mind. They used data to isolate the most high-impact use case (periodontal disease, if you’re wondering), found nearby dentists with similar profiles, and built an ultra-targeted campaign around that. That’s the model: segment → insight → data → message → scale.

“Shiny Object Syndrome” is real. And AI makes it worse.
Jordan dropped a line I loved: “This is an SOS message from Go-To-Market Jesus.”
We’re all drowning in tooling. The winners will be the ones who define problems narrowly and use AI to solve that specific thing — not boil the ocean.

Want to get started? Ask your SDRs.
Seriously. Sit down with them. Ask what research they’re doing. You’ll find gold. Then, use that to build your first microagent, Clay workflow, and AI-powered segment. Don’t start with the tool. Start with the customer.

This episode is a firehose. But it's worth a listen if you’re in marketing, sales, or running GTM.

And if you want to learn more from Jordan, find him at blueprintgtm.com or hit him up on LinkedIn.

On What Buffer and Spotify Can Teach Us About Surviving the AI Org Shakeup

AI isn’t coming for your job. But it is coming for your team structure.

If you’re leading a marketing team right now, you already feel it. The pace of AI innovation, the flood of new tools, and the sense that everything is and will continue to change at a blinding speed.

Thankfully, we don’t have to start from scratch. Nearly a decade ago, Buffer and Spotify reimagined their team structures in ways that feel like a guide for today. They weren’t solving for AI at the time. They were solving for clarity, speed, and adaptability. Those same qualities are exactly what modern marketing teams need to thrive in an AI-driven world.

How Buffer Did It (Before It Was Cool)

Buffer began like most startups, with one big team trying to do everything: product planning, design, development, and support. In the early days, it worked. But as the company grew, that structure started to break down. Priorities collided, people were stretched thin, and progress slowed.

So they began to iterate.

First, they introduced the decision-maker model. This meant forming small, holistic teams anchored by someone who could pull the right people together and make decisions quickly. It created clarity and helped those teams move with purpose.

Then came task forces. These were temporary, project-specific teams open to anyone at the company, regardless of title or department. The focus was on skills and interest, not org charts. This approach let Buffer stay flexible, solve problems faster, and build a culture where collaboration came naturally.

Spotify’s Playbook: Structure Without Bureaucracy

Spotify took a slightly different approach. They designed their organization around squads, small, cross-functional teams responsible for a specific feature or problem. Each squad had its mission and the autonomy to figure out how to achieve it.

Spotify added another layer to keep expertise sharp and aligned. Chapters brought together people with similar roles, like engineers, designers, or marketers, across multiple squads. They met regularly to share ideas, develop skills, and keep standards high.

Then, there were guilds. These were broader communities of interest, people who wanted to connect around topics like machine learning, experimentation, or diversity. Guilds were informal and opt-in, unlike squads or chapters, but they played a huge role in spreading knowledge across the company.

Spotify’s model was brilliant because it balanced autonomy with connection. Teams could move fast without losing sight of the bigger picture.

Why This Matters Right Now

Because everything is changing again.

AI is not just another tool in the stack. It’s shifting how we work, make decisions, and structure teams… and doing all that faster than most orgs are built to handle.

What worked last year may not work this quarter. You need teams that can learn quickly, test new ideas, and move without waiting on layers of approval.

This is exactly what Buffer and Spotify were optimizing for years ago. They just didn’t have the benefit (or the chaos) of AI.

Here's why their models still apply:

  • Agility is essential. Small teams can explore new AI tools in real time: content generation, customer insights, or performance optimization. They don’t have to wait for permission.

  • Expertise still matters. Role-based chapters make sure your top talent stays on the cutting edge and shares what they learn, keeping the whole team sharp.

  • Change should be expected. Buffer’s willingness to evolve shows that structure isn’t sacred. If something stops working, change it. Test. Learn. Adjust.

Designing a Hybrid Model for the AI Era

So what does this look like in real life, especially for marketing teams?

It’s not about copying someone else’s org chart. We know that’s a lost cause. It’s about combining the best parts of each model and adapting them to your goals, people, and pace of change.

Of course, every business is different. Use the following ideas as a guide (like I am) to build your team into the operators of the future.

Squads vs. Chapters: What’s the Difference?

At first glance, they may seem similar. Both are ways of grouping people across functions. But their purposes are completely different:

Squads

Chapters

Formed around

Business goals or problems

Skills, roles, or craft areas

Primary purpose

Deliver outcomes, ship work

Improve skills, share standards

Structure

Cross-functional

Discipline-based

Timeframe

Medium-term or initiative-based

Ongoing

Success

Impact on KPIs or business goals

Quality of craft, alignment, upskilling

In short:

  • Squads are where the work gets done.

  • Chapters are where the craft gets better.

You might have a copywriter working in a Lifecycle Growth Squad while also participating in the Content & Creative Chapter. One is about delivering results. The other is about growing in their role.

Let’s look at some examples.

Squads with a Mission

These are small, empowered, cross-functional teams with a shared mission and accountability for results.

Squad Name

Mission / Focus Area

Example Members

Lifecycle Growth

Drive free-to-paid conversion and onboarding engagement

Lifecycle Marketer, Growth PM, Designer, Data Analyst

AI Creative Lab

Use AI tools to accelerate creative development and testing

Content Strategist, Copywriter, Prompt Engineer, Video Editor

Customer Insights

Deliver research and behavioral analysis to inform GTM

UX Researcher, Analyst, PMM, Campaign Planner

Integrated Campaigns

Plan and execute multichannel campaigns for brand and pipeline

Campaign Manager, Paid Media Lead, Email Specialist, Designer

Feature GTM

Coordinate go-to-market launches for new product features

PMM, Enablement Lead, Events Manager, Social Strategist

These squads might evolve based on company goals, product launches, or growth stages.

Chapters for Depth and Development

Chapters are communities of practice. They help people in similar roles sharpen their skills, align on tools, and grow professionally.

Chapter Name

Purpose

Example Members

Analytics & Ops

Own tooling, attribution models, dashboard templates, and experiment design

Data Analysts, Marketing Ops, RevOps

Content & Creative

Define brand voice, visual standards, and AI content guardrails

Copywriters, Designers, Video Editors, AI Specialists

Growth & Paid Media

Share playbooks for ad performance, SEO, and media mix modeling

Paid Media, SEO Leads, Acquisition Marketers

Product Marketing

Align on messaging frameworks, personas, and pricing narratives

PMMs, Enablement, Segment Marketers

Lifecycle & CRM

Develop journeys, segmentation logic, and retention benchmarks

Lifecycle Marketers, Email Specialists, CRM Owners

Chapters meet regularly to review work, host peer critiques, share experiments, and discuss emerging trends.

Go Forth and Prosper

Now, here’s the deal. All of the above are just ideas. The best structure for your team isn’t a fixed model, it never is. It should be a flexible system that evolves as quickly as your environment does.

Buffer and Spotify learned how to build organizations that learn, share, and adapt. The rest of us can pick up where they left off. If you build squads that can move fast and chapters that keep your skills sharp, you’ll have a team ready not just to survive the AI shift, but to lead through it.