This newsletter exists for two reasons.

First, I needed an outlet to learn, to express, and, frankly, to exorcise a few demons. Writing has become the practice that forces me to face what’s in my head and in front of me. Some weeks, it feels like a chore. Other weeks, it’s a release, an exorcism of the stress and the self-doubt. And sometimes (on the good weeks) it’s a celebration! 

Second, it’s meant to be a window into the life and work of a CMO. A peek into the head trash/self-doubt, the experiments, and the projects that push a team (and me) to perform.

Marketing doesn’t sit still. The only way I’ve found to keep up with the change is to write through it. My hope is that, in sharing, it helps you work through your own version of it.

Here’s what I’ve been dealing with this week:

• On the $300M acquisition, and why chasing the next win feels a lot like addiction.

• On product marketing—what it really is (and isn’t)—and why it’s the connective tissue between product, market, and revenue.

• On keeping it fresh with Joe Ciarallo, and how music, boundaries, and fatherhood sustain a career over decades.

Thanks for reading, for showing up, and for letting me work it out here each week.

♥️ kyle

On WTF is Product Marketing?

For the past three months, we’ve been rebuilding, rethinking, and retooling product marketing at Docebo. It’s been humbling, energizing, confusing, and absolutely necessary to grow a company. The best part (and the most stressful) is that you get to see how much opportunity exists between product, market, and revenue. But I’ve also fully appreciated what happens when you get it wrong, or worse, leave it completely uncovered; EVERYONE feels it.

That’s why I’ve been asking myself (and the team) a simple question: WTF is product marketing, really?

“Product Marketing” gets thrown around a lot, especially when you’re rebuilding a team, restoring trust, or trying to reinvent how your company goes to market (welcome to my world).

So, how do you define it?

Ask ten people and you’ll get ten different answers. Writing product copy and building launch decks, running competitive research, and making sales collateral.

It’s all of that. And none of it on its own.

At its core, Product Marketing is the connective tissue between product, market, and all things revenue. It exists to translate what you build into what the market buys, and to make sure customers see value once they do.

I like to think of it as operating at the intersection of four core functions:

• Product: Owns the roadmap; product marketing ensures it aligns to market needs.

• Sales: Owns revenue; product marketing makes it easier for sales to win.

• Demand Generation: Owns pipeline; product marketing ensures the story fuels demand and conversion.

• Enablement: Owns readiness; product marketing delivers the narratives, tools, and training so every customer-facing team speaks the same language.

And here’s the important part: Product Marketing is not a service team. They aren’t there just to crank out decks on request. They are a strategic partner. They connect the dots between what’s built, how it’s sold, and how it drives value.

On Pipeline and Revenue

The best product marketers support the generation of revenue, period. What’s so funny about this sentiment is that not everyone in product marketing agrees on what that actually means.

Some argue product marketing should stay closer to product (shaping narratives, feeding market intelligence, supporting launches) while leaving revenue ownership to sales and demand gen. Others (myself included) believe product marketers should have direct accountability to pipeline and revenue impact. If they don’t, the role risks being seen as “nice-to-have” instead of “need-to-have.”

In my experience, the strongest product marketers lean into revenue. They may not close deals themselves, but they make it easier for deals to close. They may not run campaigns, but they make campaigns convert. They may not own the roadmap, but they ensure it’s aligned with what buyers will pay for by:

• Own pipeline impact. They carry a number, even if it’s shared. Influence matters.

• Make it easier for sales to sell. Talk tracks, demos, competitive positioning, objection handling.

• Craft targeted narratives. Messaging tailored to segments, verticals, or markets that actually drive demand.

• Bring market intelligence back to product. Surface insights that shape roadmap and strategy.

• Partner tightly with demand gen. Align campaigns so the story fuels both creation and conversion.

Do product marketers like being measured this way? Not always. But without a connection to revenue, the role drifts into activity over impact. And I’ve never seen a company win with product marketing that isn’t accountable to the number in some way.

On Value and Adoption

And, of course, the job doesn’t stop at closed-won. Product marketers also ensure customers see value by:

• Demystify the product so complexity becomes clarity.

• Translate releases into outcomes so features always ship with a “why.”

• Support adoption and expansion by giving product a narrative that accelerates usage.

Here’s where I’ll admit I’m still wrestling with the boundaries. Should product marketing own adoption? Or should their focus stay squarely on revenue? Especially if they are also quasi-responsible for revenue?

On one hand, adoption is the product team’s job. They build the thing, and they should be compensated and measured on whether customers actually use it. On the other hand, marketing and sales are the revenue engine, and adoption directly fuels renewal and retention. So where does the line get drawn?

My current belief: product marketing sits in the messy middle. They don’t own adoption outright, but they can accelerate it. By clarifying the story, by translating complexity into outcomes, and by ensuring every release has a reason to matter.

It’s not clean. But neither is the job.

Why Product Marketing Matters

Done well, product marketing is a revenue engine. Done poorly (or left uncovered entirely), it leaves millions on the table. I’ve seen both sides.

Hiring is hard because the role is inherently hybrid. It’s contextual. It takes experimentation to find the archetype you need. But one thing is certain: someone has to do the job from day one.

Because if nobody owns the intersection between product, market, and revenue, you’ll feel it. In the pipeline. In the sales cycle. And in the customer churn numbers.

And that’s why, in the midst of reinvention, I always start with product marketing.

On the Feeling After the $300M Acqusition

When I found out Lessonly was going to be acquired for over $300 million, I thought I’d made it. That was the mountaintop moment. The kind you dream about when you’re grinding late nights, giving every ounce of energy, and telling yourself it’ll all be worth it when the company IPOs or lands a big acquisition.

And for about twelve hours, it was worth it. The wire hit, the high came, and I soaked it in.

By the next day, though, I was back in my inbox. Back to scanning for the next hill. Back to searching for “what’s next?”

It’s insanity. And exhausting.

The chase (for the next title, the next revenue milestone, the next LinkedIn announcement) shows up like addiction, at least for me. The same rush as a three-glass-of-wine dinner where you flip on autopilot. And the same crash the next morning, when you realize you’ve paid for it twice: once in the moment, and again when it steals the day after.

That cycle of chasing “what’s next?” is a feature of my job, and probably yours too. I love what I do, but I’ve learned I can spend more time thinking about the next mountain than climbing the one I’m already on.

Sobriety taught me that lesson twice over. Cutting alcohol didn’t silence the noise. It just forced me to face it. The doubt. The head trash. The relentless voice saying, “You’re not doing enough.” All of it is still there. The work isn’t in drowning it out. The work is in learning to sit with it.

Here’s what I’ve realized:

• Milestones feel good, but presence is what lasts.

• Wins are fleeting, but showing up fully—with your team, your kids, your people—compounds.

• If you don’t deal with your shit, the next win will deal with you.

So the real question isn’t: What’s my next mountain? or What’s my next win?

The real question is: Will I be present for the climb I’m already on?

On Music as a Release Valve with Joe Ciarallo

When I started Revenue Diaries, my goal was simple: to explore the real stories behind how leaders live, work, and show up for the people around them. In this episode, I sat down with my longtime friend Joe Ciarallo — someone I’ve known since our Salesforce days — to talk about fatherhood, music, wellbeing, and what it means to sustain yourself in the long run.

Joe’s story is a reminder that life isn’t just about the work we do. It’s about the practices and choices that keep us fresh enough to do that work well.

Music as a Release Valve

Joe has been playing drums since third grade. Today, he still plays in a cover band in San Francisco (with the unforgettable name Kevin!). Music isn’t just a hobby for him — it’s a creative outlet that helps him reset after the demands of work.

What stuck with me most was advice Joe got from his dad, a musician himself:

“If you want to do it your whole life, you have to keep it fresh.”

That idea applies far beyond music. Whether it’s running, writing, skiing, or any creative pursuit, the things that make us feel most like ourselves only stay with us if we put in the effort to protect and nurture them.

For Joe, music is a post-work ritual — a way to let go of the stress of the day. He compared it to exercise: you might not always feel like doing it, but you never regret it afterward.

Fatherhood as a Mirror

We also talked about how becoming a parent changes everything. For Joe, the shift was immediate:

“Now there’s another human that’s learning what life is from you. What you say doesn’t matter as much as what you do.”

Kids notice everything. They don’t just listen to your words — they model your actions. That creates what Joe calls a “mirror” effect: you can’t hide from the person you’re showing up as.

It’s a lesson that applies to leadership, too. Teams don’t just hear what their manager says; they watch how their manager works, reacts, and behaves. In both parenting and leadership, example outweighs instruction.

Boundaries and Wellbeing

Another major theme was sustainability. Joe has seen both sides of Silicon Valley culture — the “996” grind (9 a.m. to 9 p.m., six days a week) and the realization that long-term performance requires balance.

“You have to live well to be productive and work well. Not sleeping, not exercising, not eating well — you won’t get the best out of yourself that way.”

For him, that means starting mornings with exercise and creating a hard stop to his day for family time. Since moving to the West Coast, he’s had to adjust to East Coast hours, but he makes school pick-up and dinner non-negotiable. That separation matters.

East Coast vs. West Coast

Finally, we dug into cultural differences between New York and San Francisco. Joe grew up and built his career on the East Coast before moving west during the Buddy Media → Salesforce transition.

He learned quickly that what feels “normal” in one environment can be perceived differently in another. The East Coast directness that worked for him in New York needed recalibration in California, where a different style of collaboration takes root.

It’s a reminder that context shapes culture — and leaders need to be able to flex their approach.

Why This Conversation Matters

Joe’s story weaves together themes that resonate far beyond his own life:

• Keep it fresh. Whether it’s music, running, or any pursuit, the things you want to carry with you throughout your life require intentional practice.

• Live by example. At work and at home, people notice what you do more than what you say.

• Protect your boundaries. Productivity comes from sustainability, not overwork.

• Adapt to context. Leading in different environments requires self-awareness and calibration.

That’s why this episode is worth your time. It’s not just about music or work or parenting — it’s about building a life where you can show up fresh, present, and sustainable for the people who matter most.

🎧 Listen to the full episode of Revenue Diaries with Joe Ciarallo.