Revenue Diaries Entry 46

Holy hell. Talk about a chaotic week across the world, especially here in America. The headlines were unbearably loud (for good reason) and relentless. 

I’m not going to spend time writing about this week in America, because this isn’t the place. I’ll just say this: it’s extremely hard to hold the weight of everything happening out there while also showing up inside our work, our meetings, our teams, our lives. And yet, that’s what we do. We keep showing up.

This past week, I had the rare luxury of stepping away and being fully present with my team. For two days in Atlanta, forty-plus of us gathered for our first Docebo marketing offsite since I joined. 

We argued, planned, laughed, took the DiSC personality test, mapped out Q4, started planning 2026, and reminded ourselves why a strong team matters. And that’s what we are going to discuss tonight: 

• How to build a marketing offsite that actually inspires — The agenda, the structure, and the little things that made our two days in Atlanta worth every minute.

• Why AI won’t save you (but your people will) — In a world where everyone has the same tools, your real competitive edge is the team that can learn, adapt, and move faster than the rest.

When the world feels chaotic, it’s easy to get lost in all the headlines, tools, and the “what’s next” peanut gallery. But being in a room with this team reminded me: tools can make you faster, but people are what make the work matter.

Let’s dive in.

♥️ kyle

On How AI Won’t Save You, Your People Will 

We all know everyone’s betting on AI. We get it. Every company is buying tools, rebuilding tech stacks, and vendors are selling a dream of supreme automation. Meanwhile, most of us are polishing “AI-first” slides for the next board meeting.

But like most things, when everyone has access to the same tools, the only thing that matters is the people using them.

It’s not the tech that sets you apart. It’s the team that can adapt, learn, and move faster than the rest. The people who can code the new tools, figure out what matters, and apply it in ways nobody else can.

That’s why I believe the mountaintop of leadership isn’t launching a product or hitting a revenue goal, it’s working with great people, multiple times over.

This has been on my mind a lot lately. Over the past few months, I’ve had the privilege of welcoming two familiar faces back into my world. People I’ve worked with at past companies who I know can thrive in the chaos and push me (and the business).

• Bridget Conrad Harvey – I worked with Bridget at Seismic after the Lessonly acquisition, and she is a FORCE. I’ve never met anyone better at bringing order to chaos and turning big/messy/cross-functional challenges into clear paths. She’ll be building the marketing operational engine that supports our entire go-to-market strategy across marketing, sales, customer success, and revenue operations. What makes Bridget special isn’t just her ability to organize complexity—it’s the way she makes everyone around her sharper.
  

• Ben Battaglia – our new VP of Product Marketing, who I’ve worked with at both Lessonly and Seismic. Other than sharing the same birthday, we have a deep passion for all things marketing. He has the unique experience of running marketing, engineering, and product, but also has the highest EQ of anyone I’ve met. He’ll be leading our global product marketing team—shaping our narrative, strengthening our positioning, and helping define the future of everything Docebo. Ben brings something every team craves: perspective. He can zoom out and see the story we’re telling the market while also zooming in on how product decisions connect to revenue.

There’s something uniquely powerful about working with people you’ve already gone to battle with.

• You know how they think.

• You know how they communicate.

• You know how they care.

• You know the massive things you can accomplish together.

That trust compresses the time it takes to do great work. You don’t waste cycles proving yourself or translating intent. You skip right to building.

It doesn’t mean every hire should be a “round two” hire. Fresh perspectives and new energy are critical for any team. However, when you can bring in people you trust, people you’ve already built with, you accelerate everything.

And for me, it’s more than acceleration. It’s joy. Work is better with people who make you sharper, braver, and a little less stressed when things inevitably go sideways.

And last week, our marketing team gathered in Atlanta for our first offsite since I joined. 40+ people, one room, two days of energy you can’t replicate in a remote world.

It wasn’t inspiring because of slide decks, OKR planning, or “strategic direction” (🤮). It was inspiring because of how this team showed up: collaborative, curious, and committed.

It reminded me of the first email I sent when I joined in April, outlining what I hoped we’d build 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 it should make it faster and sharper.

• 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.

• Share before you’re ready. Don’t wait for perfect. Progress beats polish.

• Get clear, then commit. Clarity up front saves time later.

• Make time for life. Do great work and still have 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.

• Make our customers the heroes. Our best marketing is their story.

Five months later, this is how this team operates.

Remember, tools may help us work faster, but it’s the people who make the work matter. AI won’t save you. A team you trust, one that can learn, adapt, and deliver… together.

That’s the real competitive advantage. And if you’re lucky enough, you’ll get to work with those people more than once.

On Creating a Marketing Offsite that Inspires

When you lead a remote-first team, there’s no substitute for being in the same room. Last week, we hosted our first Docebo marketing offsite since I joined in April. Forty-plus people, two days together.

Remote work is efficient, but camaraderie, trust, and energy don’t come through the Internet. You have to create moments where people can connect face-to-face. In my opinion, meeting at least twice a year is foundational for any team that wants to build a strong culture.

What Made This Offsite Work

We didn’t just gather to work through slides because I’m not a fan of slides. We tried to build an experience.

• Group activities are a must. We mixed in workouts (OrangeTheory), game shows, and plenty of laughs. Shared experiences matter more than another presentation.

• Start / Stop / Continue. Simple but powerful—if you actually follow through. It surfaced where we shine, where we stall, and where we need to sharpen.

• Breaks, breaks, breaks. Two days with 40 people is a lot. Downtime kept conversations flowing into hallways and meals.

• Social activity on night one. A relaxed dinner resets the tone for the next day.

• Personality profiles (we used DiSC). It’s one thing to say “collaboration matters.” It’s another to help people see how they work together.

The point wasn’t to fill time. It was to create a connection.

The Agenda

We didn’t overcomplicate things. The offsite had a clear arc: connect, align, plan, and commit.

Day 1

• Kickoff and welcome to set the tone.

• Group sessions on alignment and collaboration.

• Start/Stop/Continue to capture opportunities for improvement.

• Workshops on working styles (like DiSC) to deepen team understanding.

• A social evening to strengthen relationships.

Day 2

• Recap and reflections from Day 1.

• Strategy deep-dives on GTM, operations, and product marketing.

• Planning discussions for Q4 priorities and our 2026 vision.

• Breakout discussions to drive execution plans.

• Wrap-up with commitments and next steps to carry momentum forward.

The week was about choosing the right balance of strategy, connection, and reflection. It wasn’t flashy. It wasn’t over-engineered. But it worked because it gave people clarity, voice, and shared ownership.

Dos and Don’ts of a Successful Offsite

If you’ve ever been to an offsite that dragged, you know the warning signs. Death by PowerPoint. Sessions that run long. No clear outcomes. To avoid that, I’d suggest a few lessons we learned.

• Do keep sessions short and interactive. Nobody wants to sit through a monologue. The more you involve the team, the more they’ll own the outcomes.

• Do balance strategy with connection. Strategy sessions are critical, but they land better if people also feel like they’ve built personal relationships.

• Do make space for reflection. It’s not just about planning, it’s about creating time for people to process and share.

On the flip side:

• Don’t overstuff the agenda. Trying to squeeze in every idea makes everything worse. Less really is more.

• Don’t make it a one-way broadcast. If the leadership team is the only group talking, you’ve missed the point.

• Don’t forget the follow-up. The fastest way to kill offsite energy is to let commitments fade into thin air. The real work begins when you bring those ideas back into daily execution.

The Words That Anchored Us

When I joined Docebo in April, I sent the team a short list of principles. At the time, it was just words in an email. Five months later, it’s become our operating system.

• 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.

• Get clear, then commit. Assumptions kill progress. Clarity up front saves time later. Ask the extra question. Confirm the plan. Then get after it.

• Make time for life. 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.

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

I’d rather not call them slogans or values. They’re standards. And over the course of two days in Atlanta, I saw them in action everywhere. People pushed each other to sharpen ideas. They shared drafts and half-baked thoughts without hesitation. 

You don’t build great culture through emails and Zoom calls. You build it by showing up, together, with intention. Twice a year might feel like a luxury, especially for remote teams. But if you want a high-performing, connected group of people who trust one another and move fast, it’s not a luxury. It’s a necessity.