Revenue Diaries Entry 25

Happy beginning of the week! It’s been a whirlwind over the past seven days for me. I was in Orlando for Docebo’s Inspire conference, my first full week as CMO. I met customers, prospects, and teammates. There’s no better way to get onboarded.

But this newsletter isn’t a recap. Here’s what’s inside this week:

• The exact note I sent the marketing team on day one (and why every new leader should send one)

• A reminder that sharing your real self online matters more than you think

• Why Shopify’s leaked AI memo should be required reading for every marketing team

• A conversation with Rob Joyner on anxiety, art, and the routines that keep us sane

Enjoy.

❤️ kyle

The Note I Sent the Marketing Team on My First Day

I joined Docebo as CMO a couple of weeks ago. The first day, the first week, the first leadership meeting. Honestly, it’s all a blur. But before anything else, I sent a note to the marketing team.

Not a fluffy “hello.”
Not a long-winded career recap.
Just: here’s where I stand, what I believe, and how we’ll work together.

I do this every time I take over a team. Not because I have everything figured out, but because silence and ambiguity do more damage than clarity ever will, especially when a team has experienced change.

Here’s the actual note I sent:

Hey team,

I’m here to bring clarity and consistency. To help build a marketing team that knows what it’s doing, where it’s going, and how it’s measured.

I’ve spent the last 15+ years building marketing teams in companies of all sizes. I’ve made plenty of mistakes (I'm happy to share those in due time), but I’ve also come away with a few core beliefs that guide how I work and how we’ll work together.

Improve every week.
Sharpen how we write, plan, measure, and execute. Use the tools (shoutout to the robots). AI won’t replace the work but should make it faster and sharper. Share what’s working. Keep learning.

Build trust.
Brand is what people feel when they see our name, visit the site, hear a pitch, or use the product. Every touchpoint matters. If it’s off, slow, or sloppy, it hurts. Great marketing is consistent, clear, and intentional. It builds trust and drives pipeline. It’s an asset. Treat it like one.

Share before you're ready.
Don’t wait for perfect. Get feedback early. Let others sharpen your thinking. Progress beats polish. When we share early, we learn faster and ship better.

Get clear, then commit.
Assumptions kill progress. If something matters, we should be aligned on goals, deadlines, ownership, and everything else. Clarity up front saves time later. Ask the extra question. Confirm the plan. Then get after it. This is especially important when working with teams like sales and CS.

Make time for life.
I burned out in another chapter of my career. It’s not worth it. The work matters, but so does your health, your family, and your time. I want this to be a team that does great work and still has a life. Both things can be true.

Own a number.
We’re not here to make noise. We’re here to generate pipeline and revenue. That’s how you earn a seat at the table. That’s how you have a voice in the business.

Make our customers the heroes.
Our best marketing is their story. Talk to them, learn from them, and share their wins.

Here’s what you can expect from me:
• I’ll be clear on what matters and why.
• I’ll move fast, and I’ll expect the same.
• I’ll care more about results than polish.
• I’ll be direct.
• I’ll ask you to own your work, and I’ll own mine.

We’ll talk more soon about where we’re headed. But for now, I’m excited to get going.

Why do this?

Because people want to know what’s expected. Because silence leaves room for fear. Because culture starts with behavior, and behavior starts with clarity.

Your first note doesn’t have to be perfect, but it should be honest. Give people something to hug to while you earn their trust.

If you’re stepping into a new role, send the note. If you’re already in one, it’s not too late. Stop reading this damned newsletter and start writing.

You don’t need a reorg or a rebrand to reset expectations.

Just start with the note.

On Sharing is Caring

I recently received a note from someone who read one of my LinkedIn posts.

It hit me with all the feels—seriously, I was tearing up while boarding a flight (Sorry, lady in 2B). All kidding aside, it hit me hard because of the deeply personal experience they shared and because it reminded me why sharing more than just professional wins matters.

LinkedIn can feel like a nonstop stream of career moves, product launches, and promotion announcements. But every person behind those posts is dealing with real life. The message I received made that clear. It reminded me how important it is to show up honestly.

Sharing your real self doesn't mean telling all or turning every post into a therapy session. It means being consistent with who you are. It means choosing honesty when it's easier to polish things up. That kind of sharing builds trust. It builds connection. And it helps people feel seen.

The truth is that vulnerability makes our communities stronger. It creates space for empathy. It builds bridges.

‘So here's the ask. Share something real. Doesn't have to be heavy. Just be genuine. Do it regularly. You never know who needs to hear it.

Keep showing up. Keep connecting.

On the Shopify Cultural Gut Punch and Why AI is Not Optional

Last week, I wrote about how Buffer and Spotify redesigned their orgs to be more adaptive. They didn’t know it then, but they were building for an AI future—small teams, clear missions, fast feedback loops, and deep communities of practice.

This week? We get the cultural gut punch to go with changing org landscape.

A leaked internal memo from Shopify CEO Tobi Lütke started circulating. And it’s worth reading in full, but here’s the headline:

“Using AI effectively is now a fundamental expectation of everyone at Shopify.”

He lays it out with zero fluff:

• AI must be part of every prototype phase.

• People will be evaluated on their AI usage.

• Share what works (and what doesn’t) across the company.

• Don’t ask for more headcount until you’ve explored what AI can do.

You can argue tone. You can argue feasibility. But you can’t argue this: he’s right.

Most teams (especially marketing teams) still treat AI like a productivity hack.

But the reality is more urgent. AI isn’t just another tool in the stack. It’s rewiring how work gets done, decisions are made, and teams can move quickly.

That’s why Buffer, Spotify, and Shopify all matter right now. Aside: It would be way cooler if we could rebrand Buffer to Bufferify. Anyway, they each give us part of the playbook:

• Buffer and Spotify show us how to build flexible, cross-functional teams that adapt quickly.

• Shopify shows us why urgency matters—and what leadership looks like when the stakes are high.

Here’s the part that stuck with me most: “If you're not climbing, you're sliding.”

No fancy AI strategy deck. No new organizational model will save you if the people inside the company don’t believe it.

So what do you do? Here are some quick takeaways that can be easily stolen from Tobi:

• Create an internal AI prompt library. Shopify uses Slack and Vault. You can do the same with a shared doc and a channel like #ai-lab.

• Make AI part of onboarding. Give new hires the tools, examples, and prompts you use.

• Add AI usage to performance reviews. Not as a threat. As a signal: this is part of the job now.'

• Prototype with AI first. Campaign concepts. Landing pages. Research. Make AI the first draft, not the last resort.

Last week, I said structure needs to evolve. This week, I’ll say it louder: So does the mindset.

Because if AI isn’t optional for Shopify employees, it sure as hell isn’t optional for us.

On Anxiety, Art, and Addictive Routines with Rob Joyner

There’s a moment in every interview where I’m impressed. Not because of my guest's career accolades but because of the individual's true sincerity and creative genius.

That moment hit early with Rob Joyner.

He’s the co-founder of a legal tech company called Centerbase. But when he’s not building software, he’s covered in paint, layering abstract art in a studio he built behind his house. And I’m not talking about a side hobby. I’m talking about the kind of art collectors commission, filling gallery walls, and sitting across from Ferraris in million-dollar garages.

And yet, he still wakes up at 4 a.m. to paint before anyone else is up. Not for the money. Not for the audience.

For the clarity.

Rob’s work is layered… literally. He throws plaster and paint onto canvas from every direction. It’s his version of therapy. A way to quiet the anxious swirl of being a dad, a founder, a leader. The work, the chaos, the noise…

It’s all in the painting.

He didn’t go to art school. He didn’t plan to be a painter. A friend told him to buy a canvas to fill a bare apartment wall in college. He walked into a Michaels. He hasn’t stopped since.

And like many of us who build things, Rob has what he calls an “addictive personality.” When he enjoys something, he goes all in. He used to wake up on Saturday mornings obsessing over whether he’d sold something by 8 a.m. If he hadn’t, he was grumpy. Distracted. Stuck.

So he set some rules.

No painting on weekends. No work in the studio when the kids are around. No notifications on the phone. Bed by 9 p.m. Most days, he’s up by 4. Paints for a couple of hours. Then moves on with his day.

He treats painting like a job. Because it is, but more importantly, it’s a safeguard. It’s what keeps him centered.

He told me he has no plans to leave the business world. He loves balance. If anything, he wants to bring his two worlds (art and tech) closer together but not merge them entirely.

Some passions are better left unoptimized.

Toward the end of our conversation, we talked about parenting and what it means to truly be present. Rob said the studio sits in his backyard. He walks across the grass and into the house after work. The transition from founder to father happens fast. There’s no commute buffer, so he forces himself to be intentional.

Same.

We talked about guardrails… about how people like us need them. Because if we don’t create boundaries, we’ll slip. We’ll grind. We’ll check email at dinner and justify it as productive. We’ll bring the bad mood from LinkedIn comments into bedtime stories. We’ll keep searching for momentum when what we actually need is stillness.

Rob reminded me of something I’ve been trying to practice: envisioning yourself at 80. Looking back on this exact stage of life, noticing the kids, the chaos, and the tiny, blink-and-you-miss-it moments that might be easy to skip now but impossible to get back later.

Listen to the full interview here.