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The more time CMOs spend implementing AI, the more human the conversations become.

Super Huddle in Silicon Valley last week reinforced this. We covered tools, tactics, experiments, strategies. All valuable. But three moments stood out as deeply human stories about trust, change, and leading people through transformation.

Denise Persson (CMO of Snowflake) and Chris Degnan (former CRO) sat down with Drew Neisser for one of the best fireside chats I’ve seen. Nine years together, four CEO changes, zero to billions.

Their book “Make it Snow” tells the story, but the partnership is what stayed with me. No daylight between sales and marketing. Issues resolved behind closed doors. When they came out, they were aligned.

They had each other’s backs and called each other out. Intensely customer-driven with deep trust.

This reinforced something I see in my work. Early alignment between sales and marketing can be the difference between scaling and failing. When hiring, prioritize cultural fit, urgency, and adaptability over where people worked before.

Kate Bullis (ZRG) and Hugh Marshall (Hedrick) both said executive recruiters aren’t being asked for AI expertise in CMOs right now. They want leaders who know how to drive change.

This didn’t surprise me. The hardest part of AI adoption isn’t the tech. It’s shifting how people think and work. We are the hardest part.

Kate’s advice resonated. Lean into your strengths as CMOs. We’ve been through transformations before. We know how to do this.

I keynoted on human + AI organizational transformation and co-facilitated four roundtables with Samantha Stark. We covered experiments, tools, use cases, KPIs, and how teams are reorganizing.

But the conversations that resonated most were about upskilling teams, inspiring what’s possible, meeting people where they are, and leading with compassion and confidence.

And giving ourselves grace. We need to take care of ourselves as we lead through this.

The fundamentals of leadership haven’t changed. But AI removes any room to ignore them.

The best part of the weekend was meeting new people and reconnecting in person. The conversations between sessions, the shared “oh god, us too” moments, the energy you can’t get over Zoom.

Big thanks to Drew Neisser and the CMO Huddles team. To all the inspiring speakers and to every CMO who showed up and shared openly. I’ll try to tag you in comments but I know I’ll miss many (I need a little grace here ;-))

Still processing so more to come. Looking forward to continuing these conversations.

(And yes, there were breakdancing penguins there. See link in the comments to see my previous post with video. If you’re going it alone, find your huddle.)

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One surprise creates a story people share. Systematic surprise creates trust. That’s what made Eleven Madison Park number 1 in the world. Not better food. Every top restaurant had exceptional food.

Will Guidara was on Oprah’s recent podcast talking about his philosophy of unreasonable hospitality. If you caught his keynote at Pavilion’s GTM2025 or read my newsletter about it, this conversation goes even deeper.

Listening to it, something landed differently this time.

I’m a sharer. Always have been. I don’t know any other way.

In some corporate environments, that wasn’t trusted. Sharing perspectives to make something better got misconstrued as positioning or having a personal agenda. Offering a different angle became “unsolicited advice.”

But this is what I believe: When you chase butterflies, they fly away. When you build something valuable and share it openly, the right butterflies come to you naturally. Not all of them, just the ones that align with your values and vision.

People tell me there’s something unexpected about my content – the depth, the openness, how it goes from strategy to action. They tell me they feel seen, empowered, like they can actually do this with or without my help. Last week someone said, “You changed the trajectory of my career.”

My passions come first: elevating the strategic value of marketing, using business as a force for good, ensuring diverse voices at every table. AI is the amplifier. It’s simply the means to that end.

Turns out, that attracts the right butterflies. That’s exactly what Will understood. His team spent the “foolish 5%” of their budget on experiences that created lasting memories. Not because it was efficient. Because it’s what people remembered.

In the AI era, everyone will have access to the same tools, the same playbooks, and the same “best practices.”

What they can’t copy is how you made people feel.

Maya Angelou was right. People forget what you said. They forget what you did. But they never forget how you made them feel.

See the comments for the link to Oprah’s podcast with Will Guidara.

If you want the B2B translation, I also put in the comments the link to my newsletter on building moats through unexpected experiences with AI.

Happy Sunday. ☕

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Take that, Sora! Let’s see you generate a video of breakdancing penguins with 50+ CMOs cheering them on in the heart of Silicon Valley.

Last night at CMO Huddles Super Huddle dinner, this happened. Penguins doing backflips, headspins, and backspins on the dance floor. 🐧 It was flocking awesome!

The penguin is more than just a mascot for this CMO community. It’s the entire philosophy.

Drew Neisser (the self-proclaimed “Penguin-in-Chief”) built this community on the idea that CMOs, like penguins, survive harsh environments by huddling together. They communicate. They adapt. They lean on each other when the pressure’s on.

Yesterday I keynoted on human + AI org transformation and facilitated strategy lab sessions with Samantha Stark, Kathie Johnson, Jamie Gier, and Bob Wright. Today’s another full day of learning with some of the sharpest marketing leaders in B2B.

More insights next week. If you’re going it alone right now, find your huddle.

BTW, Sora took me up on the challenge. See the link to the Sora video in the comments. Wow, I can attest that we were a lot more fun than the stiffs in Sora’s video. And what’s up with all the cheering sound effects when everyone’s sitting like bumps on a log. 🤣

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ChatGPT turns 3 years old this month! Some GTM leaders are still asking “What AI should we use?” This timeline answers a better question: “What kind of work are we ready to do with AI?”

The timeline looks chaotic. But it shows aggressive progression through three stages of adoption.

► 2023: Using AI as Tools

ChatGPT gave us a blank text box. Teams spent the year experimenting with individual tasks like writing, research, and problem-solving. The wins came from better prompting.

GPT-4 brought multimodal capabilities and better reasoning. Teams got more ambitious with what they asked AI to do. But AI was still something you used for isolated tasks. You asked, it answered, you moved on.

► 2024: Building and Guiding AI as Teammates

Custom GPTs took off because generic AI wasn’t enough. Teams needed AI that understood their specific context, frameworks, and voice.

Claude 3 brought advanced reasoning. Deep Research and agent capabilities launched. AI Overviews, Artifacts, and NotebookLM showed how AI could synthesize across sources and handle multi-step workflows.

This was the fundamental shift. Teams moved from asking questions to defining roles and handoffs. AI became something you collaborated with, not just consulted.

► 2025: Orchestrating and Governing AI Systems

Multi-AI workflows are here. Specialized AI teammates can work together on complex projects while humans focus on strategy and high-level decisions.

GPT Agents, voice and vision integration, and tools like Veo 2 and Sora 2 are pushing what’s possible. The work now is figuring out how multiple AIs coordinate while humans guide the outcomes.

Your team is somewhere in this progression. Figure out where you are, upskill your team, and reimagine work with AI.

Moving from tools to teammates to systems requires clear thinking about workflows, handoffs, and what problems you’re solving. The timeline shows what’s possible at each stage. Use it as your roadmap.

I also cover this in more detail in my newsletter on moving from org charts to work charts. See link in the comments.

AI adoption works when you build capabilities that strengthen your team and improve your work. Focus on that. The tools will follow.

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