Revenue Diaries Entry 44

Cheers from South Haven, MI! I hope everyone is enjoying their extended weekend. I know I am.

This week’s Revenue Diaries is about relevance. On one side, it’s personal: what happens when the things that used to define you, such as parenting, career wins, and the “look at me” moments, start to fade? I call it the dark cloud of irrelevance, and it sneaks up on all of us eventually. David Brooks refers to it as the second mountain. Whatever you call it, it’s that shift from chasing to digging deeper.

On the other hand, it’s professional: we've asked AI to run our marketing. Spoiler: it didn’t. However, along the way, we learned what AI is actually good for, what it’s not, and why the real value lies in moving from button pushers to system builders. The flattening is here, and the only way through is curiosity and experiments.

So whether you’re still climbing your first mountain, staring at the second, or just trying to figure out how AI changes your job, I’m excited you are on this journey with me.

♥️ kyle

On the Dark Cloud of Irrelevance in Parenting & the Job

I was sitting on the front porch the other night when my kids rode off on their bikes to play with the neighborhood kids. They didn’t look back. There wasn’t a “Dad, can you come?” There wasn’t, “Watch me!” They just pedaled away, completely fine on their own (with their Apple Watches keeping them connected, ofc).

I felt a strange mix of pride and unease. Pride because that’s the point of parenting, right? To raise kids who don’t need you every second. Unease because, in that moment, there was an instant disconnect between my kids’ independence and my own self-worth: If they don’t need me, then who am I?

And this goes beyond parenting. The same question sneaks into careers. What happens when the meetings feel more predictable? When the milestones that once thrilled you start to blur together? When the chase that defined your 20s and 30s doesn’t carry the same weight in your 40s?

I’ve written three books (two from Wiley and one from Pearson). I’ve started and run an agency. I’ve presented at over 300 conferences with crowds ranging from 15 to 2,000. I’ve traveled the world for my job, from Sydney to Munich. I’ve experienced an IPO and then an acquisition. I’ve helped build a company that was bought for $300 million. I was a Forty Under 40 recipient at 24, one of the youngest ever in Indianapolis. I’ve led teams from 10 to 100.

And yes, even with all of that, the feeling still creeps in. Which can only mean this can’t just be me, it’s a universal feeling. Professional athletes feel it when they retire. Veterans and police officers face it when their uniforms come off. For years, your identity has been built on being that person… and then one day, you’re not. 

Welcome to the dark cloud of irrelevance.

And that dark cloud could be threatening if you don’t proactively manage your mental health. You don’t want to start feeling like an afterthought, a footnote in your own story.

Which is absolutely insane if you think about it. 

David Brooks calls this moment the beginning of the “second mountain.” The first mountain is all about proving yourself: climbing the career ladder, building independence, chasing achievements. And while it’s necessary, it’s also shallow. The trophies and titles rarely satisfy for long.

For those of you reading in your 20s and 30s, take it from me. It’s true. 

The second mountain is different. It’s not about climbing higher; it’s about digging deeper. It’s built on commitments to people, to a cause, to a faith or philosophy, to a community. It’s the shift from me to we. From happiness (which is fleeting) to joy (which is sustaining). 

The strange thing is that most people only find their second mountain after a loss, a failure, a sudden realization that the first mountain wasn’t enough, and it just creeps in, one quiet evening on the porch.

I’m not there yet, but I can feel the ground shifting. And it makes me wonder: what does relevance look like in your 40s, 50s, and beyond? How do you reinvent without clinging to what used to define you?

So if you’re in your 20s or 30s chasing the first mountain, go for it. Build, achieve, prove yourself. But know this: at some point, that mountain ends. The real test isn’t whether you can climb it, it’s whether you’re ready for the valley, and whether you dare to start the second climb.

On We Asked AI to Run Marketing. Here’s What Happened. 

A couple weeks ago, our VP of Revenue Marketing (Silvia Valenia) and I stood on stage at the Highline Conference in Jackson Hole with a simple opening line: “We asked AI to run marketing. It said good luck.”

That’s really the story right now. Everyone wants to know:

• Are our jobs in danger? Not yet. Well, maybe.

• Are our jobs changing? Hell yes.

• Will hiring slow down? Yep.

• Will team structures change in the next 12 months? You bet.

The short version: AI isn’t coming for your job, but it is coming for the way you do your job.

From Button Pushers to System Builders

Most marketing organizations today still resemble a channel-by-channel machine: email, social, and paid search specialists. The “button pushers.”

However, as AI infiltrates every workflow, the value shifts. It’s less about pulling levers and more about designing, testing, and running systems.

This echoes something I wrote recently about the Great Flattening of Product Marketing. In this entry, I argued that PMM is under pressure to do more with less. Layers are being stripped away, and suddenly one person is responsible for what used to be the work of three. The role shifts from being a translator or messenger to being an influencer, strategist, and builder.

The same flattening is happening across the rest of marketing and AI is accelerating it. You don’t need a dozen narrow roles pushing buttons; you need fewer, sharper people building systems that span channels, capture insights, and scale experiments.

So the question isn’t whether your team will flatten. It’s whether you’ll flatten with intention—by shifting talent toward curiosity, experimentation, and influence—versus letting AI and budget pressure flatten you by default.

So, what the hell are we actually doing with AI? 

A fair question, which is why I asked Silvia to present with me. Over the last eight weeks, our team has run over 12 AI projects. Some were wins, some were flops, all of them were learning experiences.

Here’s a taste:

• Audience insights from calls (UnifyApps).

• Personalized account pages (Tofu).

• AI-powered website copy (Webflow).

• Revbot for on-the-go insights.

• AI reporting through Dreamdata and Hockeystack.

• Even AI-driven homepage copy and a website bot trained on our data.

The reality: only one of those projects was a homerun. But the lessons? Priceless. Thanks, Mastercard. :) 

What Worked vs. What Didn’t

Working:

• AI insights that fuel better marketing at scale.

• SEO/GEO tools for content acceleration.

• Speed and execution over waiting for ROI.

Not Working (yet):

• AI reporting (data is messy).

• AI website bot (needs a lot more value).

• Website copy experiments (numbers not trending right).

• Getting the entire team to integrate AI into their daily work.

The win isn’t the flashy tools. It’s the insights.

Three Lessons from the Trenches

1. Volume + speed > ROI. If you expect every AI project to be a homerun, you’ll quit too early. One out of 12 was a hit, and that’s a huge win.
   

2. Timebox everything. Don’t get lost in endless measurement loops. Run the experiment, gather the learning, and move on.
   

3. Build a culture of experimentation. Every marketer on my team has to run two AI projects per quarter. Curiosity isn’t optional.

How to Start Today

If you’re staring at AI from the sidelines, here’s how to dip a toe in without blowing your budget:

• Mine the hidden insights you already have: Gong, Chorus, Looker dashboards, GPT.

• Get visibility into AI search tools like Xfunnel or UseBear.

• Negotiate free or cheap access to AI tools. This is the era of the POC.

• And if you’ve got no budget? Take bold bets with traditional paid media while you wait.

Here’s the deal, AI isn’t replacing marketers. But it is replacing slow marketers. The only way forward is to conduct more experiments, faster, and build teams that prioritize curiosity as a key job requirement.

That’s what we’re doing at Docebo. And so far, the most important lesson is this: AI won’t set you apart. Your people will.