Last week, I told you I'd know by Tuesday night if we got Inspire (our user conference) right.

And wow, I went through every emotion from the moment I published the newsletter last week to today, where I’m writing you from my flight back to Indianapolis. My voice is shot. My immune system is pissed off. But among all the head trash and sinus pressure, there’s accomplishment… the feeling of exuberance and relief after finishing something extremely hard. 

So, did we nail it? 

I would say yes. Not all of it, ofc, but most of it.  

This was the first time I've supported a thousand-person conference as a CMO. The first time I've helped create something that has to matter for customers, prospects, analysts, partners, board members, the market, and our own team... all at once. 

The night before the Tuesday keynote, I barely slept. I’d close my eyes and imagine every possible scenario that could go wrong: demo issues, slides not animating, wrong videos playing at the wrong times, lack of energy in the room, what would the board think, what would my CEO think, etc. etc. etc.

SPIRAAALLLINNNNGGGG.

I’d also try to force myself to think of all the GOOD that could come of the keynote. Here’s a shocker: it didn’t help.

I eventually popped a sleeping pill at 3 am. (I do not recommend this, especially when you're waking up at 5:30. But, you know... YOLO.)

Keynotes are stressful, but there is a special kind of stress when you are a public company. The conference is our Super Bowl, and the keynote is the halftime show. The story you tell that day is the foundation for everything else at the conference and a lot of what you tell the market for the rest of the year. So, the couple of hours of medically induced sleep helped a little, but not much. 

So, while last week’s entry was a bet. I thought this week could be a post-mortem.

Fourteen lessons I'm taking with me from Inspire 2026 to make Inspire 2027 that much better. Some of them came from things that worked. A few of them came from things that didn’t.

All of them come from the heart. xoxo kisses.

♥️ kyle

Lessons Learned Running a 1000+ Conference

You just want the lessons, right? I don’t need AI to draft the preamble, and I sure as hell don’t need to spend time writing it. Let’s get into it. 

1. Be in the room. Actually in the room.

This is the lesson that earned the top spot, and it's the one I'm most pissed about.

Multiple people on my team mentioned it during the conference. Some version of: "We've never had a CMO actually help with stuff." I was helping set up. Helping tear down. At one point, I was sitting on the floor pulling tiny plastic bags off the pins we were giving out at registration.

That's not a story about me being a great leader. I’m far from it. That's a story about how low the bar apparently is. And it pissed me off.

If you want your team to feel ownership... if you want your customers to feel something real when they walk into the room... you cannot be the CMO who flies in for the keynote and gets escorted to dinners. You have to be there the night before, on the floor, asking what's broken. You have to know which booth lost a power cable and which session room has f-ed up Wi-Fi. In our case, it was the entire hotel. 

And yes, you have other responsibilities, but your top priority should be the damned event. Not the dinner, or the analyst meeting, greeting board members, etc. Sure, all of it matters, but none of it will replace being there with your team and ensuring the experience is GREAT. 

You're not above any of it. That's literally what you're paid for.

2. The keynote is not part of the conference. It IS the conference.

Everything else builds on top of it. The story you tell on the keynote stage is the story your audience tells back to you for the next three days, and to the market for the rest of the year. (Well, maybe the next three months. Thanks, AI.)

Most CMOs don't appreciate the weight of it, I sure didn't.

Which is exactly why the keynote and the analyst content have to be locked two weeks before the event. Not "mostly locked." Locked. The two weeks before the show should be about rehearsal and polish, not figuring out what we're saying. If you're still writing the keynote two weeks out, you've already started too late.

I know what some of you are thinking. Kyle, our engineering team just became 50% more productive thanks to AI. We're shipping more product than we ever have. The story is changing every week. How do you lock content two weeks out when the company itself is moving that fast?

Oh, wait… that was just me talking to myself. Well, Kyle, fair question. I have the same feeling.

This is the balance in my head at the moment, and after walking out of the keynote room. Speed and story are two different problems. Engineering is shipping faster because of our robot friends, and they should keep shipping. But the keynote shouldn’t be a long feature this and a “look at how great we are” listicle. The keynote is a narrative... a thesis about where the company is going and why the market should care. That story should not change every week, even if the underlying product does.

If you can't lock the story two weeks out, the story isn't tight enough yet. That's not an AI problem, that’s a you/we problem. Get clear and double down on the narrative.

3. Build the keynote around rhythm, not content

The instinct is to think about a keynote as content. What are we announcing? What's the story? Which features make the cut? Which acquisitions get the most airtime?

All of it matters, but what actually keeps a thousand people leaning forward is rhythm.

We rotated people on and off the stage: our CEO, SVP of Product. the CEO of 365Talents (the skills intelligence company we acquired in January), the CEO of Zive (the company we announced acquiring the morning of the keynote), our CTO, and our Chief People Officer. 

Next year, we are going to spend more time weaving customer stories into the keynote. But the constant movement is something that I highly recommend you try. 

When you have one person waxing poetic for too long, everyone starts checking their phones and wondering, “Who did Debbie go to dinner with last night?” When you shake it up and move people in and out, they are more likely to stay focused. 

We may have over-rotated too much this year, but we can always make it better next year. I believe the pace is a silent killer of a keynote, and most teams don’t pay enough attention to it. 

4. Lean toward live demos. Even when it scares you.

Live demos stress me the hell out, but you cannot replicate the experience with a recorded one. People know. 

Hell yes, it’s a riskier choice. Something could go wrong, and you're trusting your engineers and product team to perform. 

It's also the choice the audience will remember.

Audiences can feel the difference between "the marketing team produced this video" and "this person knows the product so well they're going to walk us through it in real time." The risk is part of the value. When it works, you've earned true credibility. 

And if it doesn’t work? The audience is usually on your side. They want you to make it through. Doesn’t mean you slouch off, just means you balance your stress accordingly. 

5. Add in small WOW moments

Toward the end of our keynote, we brought Boston Dynamics on stage with Spot, their robotic dog. Spot danced and we connected Spot with the learning use case which drives the training around using Spot in warehouses all over the world. 

The moment was directionally tie to our product, they are customers afterall. But it was more focused on the experience we wanted people to remember. 

Most keynotes are people in dark clothing on dark stages talking about market changes and demoing software. That is the baseline. The thing that makes a keynote stick is the moment that breaks the pattern.

If you don't build at least one wow moment into your keynote, you're handing the audience a forgettable show. They'll remember the venue. They won't remember you.

And come on, you are irrelevant as a marketer if they don’t remember. 

6. Pick a keynote speaker from outside your industry with an interesting story.

This one I've made a deliberate decision on for years. If you have the budget for a speaker, do not pick another technologist.

We had José Andrés at Inspire, the restaurateur, chef, and philanthropist. Food connects deeply to Docebo. We're an Italian-rooted company, our CEO is wildly passionate about cooking, and there's something universal about the way Jose talked about feeding people during disasters. I’ll bet $100 that AI wasn’t mentioned once in the conversation. It wasn’t about technology and software; it was about the most important thing: our humanity.

I made the same call at Lessonly years ago when we brought in Guy Raz from How I Built This, when he was earlier in his podcasting journey. Same thinking and it generated the same results. We didn’t need someone droning on about learning technology; we needed a great storyteller, and Guy delivered.

The safe move in anything in life is usually the forgettable one. 

Pick someone the audience didn't see coming. Someone who can pull on a string that the rest of your conference can't reach.

7. Product marketing and product management have to be at the center, not on the periphery

This might sound obvious, but I’ve found it’s not. 

Most events teams I've seen run conferences and "loop in" product marketing two weeks before the keynote. They treat product marketing as a contributor instead of a co-owner. And it’s f-in backward.

Anything that touches messaging, positioning, customer story, prospect narrative... product marketing has to be at the center of it. 

Like any extremely hard project with a ton of stakeholders, it will strain the team. But the alternative is a conference where the storytelling and the product story aren't connected, and the audience can feel it instantly. Believe me. 

I think the same goes for product management. Our product team and product leadership were in the building from the start. They also hosted hundreds of customer meetings. The customers have heard, and we got more product feedback in three days than we'd get in three months of structured research.

Pro tip: place somebody in charge of managing/setting up/ organizing meetings between your customers and product leadership. Make it someone's goal. You will not regret it. Because if your product team isn't booked back-to-back at your user conference, you wasted a flight.

8. Build a pre-conference education & enablement day

This is a must-do for anyone in technology, especially enterprise technology. 

It can show up in a variety of ways but at Inspire it was Docebo University. About half the attendees showed up a day before the conference to get certified, get hands-on with the product, and spend time with our solutions consultants and product team.

I believe it helped set up the positive energy for the entire conference.

The people who came through DU walked into the keynote already grounded in the product and they were already primed for more announcements, learnings, etc. 

Even if you don't have the resources to run a full day, carve out pockets of time before the welcome reception. Get your solutions consultants and product team in front of the customers and admins flying in early. Culture and loyalty are built through these sessions, not necessarily the keynote. 

9. Introduce a physical swag store. Not a swag bag.

This is the fourth company I've built a swag store for and I'll keep doing it. We have the Never Stop Shop at Docebo, and we HAD to host a pop-up shop at the conference. It’s a must.

At Inspire, every attendee got a gold Inspire coin at registration. Take the coin to the booth, redeem it for the swag of your choice. At Lessonly, we did it differently. The app awarded "llama bucks" for completing activities, which you could spend in the store on Lessonly merch.

Honestly, the form doesn’t matter one bit, just do the damn thing.

Who wants another random t-shirt thrown into the bag at registration? Nobody. It also has a 50/50 change of ending up in the trash or at Goodwill. A physical swag store is an experience. People get to touch the product, they get to talk to a human and actually choose the product and the swag becomes something they actually want, not something they were given.

You're a marketing team. You should know better than to outsource one of your most physical brand touchpoints to a registration desk.

10. The brand has to feel like one continuous experience

Color palette. Signage. Booth design. Screen placement. The pillows on the hotel furniture. Yep, I’m being serious. I love a good branded pillow. All of it has to feel like one experience, not a collection of branded moments stitched together.

We treat Inspire as its own brand identity that's connected to but distinct from Docebo. The conference has its own palette and it’s own tone. That gives us room to do things that wouldn't make sense within the day-to-day and lets the conference feel like a destination. You want it to feel like a destination, an experience! 

If you're running a conference, build it like its own brand. The first impression isn't the keynote. It's the moment they walk into the lobby and see the color, the booths, and the signage.

11. Acquired companies need to feel native, not bolted on

When you acquire a company and bring them into your event, their booth, their visual identity, and their experience all need to feel connected to your brand. Otherwise, the audience reads it as two companies sharing a venue.

We had 365Talents on the floor. The integration didn't blend the way it needed to. It felt adjacent to Docebo, not part of it. That's a fixable problem, and one I'm carrying into 2027.

The lesson is bigger than booths. When you acquire a company, your conference is one of the loudest signals to the market about whether the integration is real. If the booth feels separate, the acquisition feels separate. And believe me, this acquisition is not separate; it’s integrated. 

12. Executives are hosts, not rehearsers

This is the one we’re rebuilding the run of show around for next year.

Our keynote rehearsal ran late. Long enough that some of our executives didn't make it to the welcome reception. No bueno.

Rehearsal matters, but so does the moment when customers walk in for the first time and look around for someone they know.

If your executives are stuck in a ballroom running through slides, they are not hosting. And you've squandered the most important hour of the night.

Don’t squander it. It’s definitely on my list to fix next year. The run of show has to protect executive floor time during reception. If they have to rehearse, they don't all rehearse together. You distribute their time so somebody is always in the room with the customers.

13. Food & beverage proximity is brand experience. Not catering.

When people walk out of a session, food and drink need to be right there. Not down a hallway. Not at the other end of the venue. Right there.

The moment a session ends is when energy is highest and conversations are starting. If your audience has to hike to find a coffee, the energy will die a slow and painful death.

The closing party is the same principle on a bigger scale. The night people remember has to feel like a night, not a logistics exercise. Long food lines kill momentum. Limited variety kills momentum.

I mean it feels over the top but this isn’t catering, it’s experience design like everything else. Treat the food and the flow with the same care you treat the keynote slides.

14. Recognize your team. By name. Specifically.

Before I started this entry on my flight home, I spent some time drafting a thank you note to the marketing team members and what they had done to make Inspire successful. I asked my leadership team to fill in any gaps so I didn't miss anyone. It took most of the morning. It was the best thing I did all week.

A conference is built by the people who were up at midnight tracking down a partner package that got delivered to the wrong hotel. The people arguing with the AV team about why a confidence monitor wasn't loading. The people on the floor hand-pulling plastic bags off pins while the rest of the company was at dinner.

You can't recognize what you didn't see. And you can't see what you weren't close to.

Lesson #1 and Lesson #14 are the same lesson, really. Be in the room. Pay attention. Make sure the people who built it hear from you, by name, that you saw them.

Do that consistently and you'll never have a hard time hiring great people. Word gets around about the leaders who actually see their teams.

On What's Next

Alright. So, you are probably still wondering how it went. I’d say great! 

The energy in the room was real, and people were engaged. The entire Docebo team showed up. I mean, really showed up.

Three days ago, I didn't know if we got Inspire right. Now I do. Most of it, but not all of it. But I know what we bet on. I know why. And I know exactly what I'd burn down and rebuild.

Ciao!