Revenue Diaries Entry 28

“You ask too many questions. Come with the solution.”

That’s what I told Alex Adkins during a 1:1 at Lessonly.

At the time, she had just transitioned from the BDR team into a field marketing role. Katie Brunette (our Director of Brand & Events at the time) was on maternity leave, Yellowship (our biggest event of the year) was looming, and Alex was reporting directly to me.

She navigated many new responsibilities and did what most smart, high-performers do when thrown into the deep end… she asked questions. 

Lots of them.

But in that moment, I gave her some direct feedback that in hindsight feels a little harsh but ultimately worked… 

Constructive feedback is important because, usually, it’s not easy to hear, but it will unlock something inside high performers. 

She thought collaboration meant asking for approval. What she learned is that leadership means expressing a point of view.

That single feedback became a pivot point in her approach to her role and her leadership today.

Alex is now building Planwell, an incredible event services company supporting marketing teams around the world. I’ve worked with her and her team in three different jobs, and they’ve delivered every time. She’s an entrepreneur, a badass, and one of the most thoughtful marketers I know.

She recently wrote about that 1:1 and what it meant to her. It’s worth a read:

The best feedback isn’t always the softest (it shouldn’t be). But it is the kind that changes how you show up.

❤️ kyle

On Speaking the F*ck Up: A Conversation with Jen Allen-Knuth

I’ve followed Jen Allen-Knuth on LinkedIn for a long time. She's one of the best voices out there, not just in sales, but in showing up with honesty, depth, and the kind of humor you actually want to hear at a kickoff. So, of course, I had to get her on the podcast.

But we didn’t talk sales strategy. We talked life. And dogs. And social anxiety. And being a stepparent. And grief. And why we both probably care more about dogs than humans (Jen has four rescue dogs and a ferret named Ernesto DePantolano, so you be the judge).

Here are a few highlights:

The Discomfort Behind the Persona: Jen’s one of the most engaging people online, but she admits real-life events drain her. “I’m a wall clinger,” she told me. It’s a reminder that confidence on camera doesn’t always translate to confidence in a room—and that’s okay.

Why Her Stepkids Changed Everything: Jen never planned to have kids. Then she met Nick, who had four. Two had lost their mom at a young age. “It made me realize how little separation I had between work and life,” she said. “Now, I hear the front door open at 3 PM and it snaps me into being present.” She doesn’t want to “mess this up” a phrase she repeats often, with real weight behind it.

Grief and Dogs: Her dad, who passed a few years ago, grew up in the foster system. He didn’t talk much about it—but when he started rescuing dogs late in life, something clicked. “I think he saw himself in them,” Jen said. Now she posts every week about shelter animals and raises money through her platform. It’s not content for clicks. It’s content that makes a dent.

Starting Her Own Thing: After multiple jobs, Jen finally launched her own business called DemandJen. It took a push from Amy Volas, who told her, “When are you going to work this hard for yourself?” The answer: now.

Advice to 21-Year-Old Jen: “Your ideas aren’t as bad as you think they are. Speak the fuck up.”

There’s a lot more where that came from. Listen to the full episode here 

And do yourself a favor: follow Jen on LinkedIn. Then go adopt a dog.

On How to Talk Like a CMO: A Guide to Communicating to Your Boss

Markerets are wired to motion. We love moving! We switch context a hundred times a day. We ship. We hustle. We take pride in to-do lists that never end.

At least I do. 

And early in your career, that hustle often looks like this:

• Schedule social posts

• Build landing pages

• Pull reports

• Write. Write. Write.

• Update nurture flows

That kind of output gets you noticed but only noticed. You have to go one step farther. You have to communicate the impact of what you do—not just the effort.

Your bosses. The VPs and CMOs… aren’t evaluating your success based on volume. They aren’t being judged on volume either (or at least shouldn’t be). They’re listening for outcomes, strategic thinking, and business alignment.

Just like you have to translate marketing speak into boardroom speak, you also need to translate tactical tasks into strategic updates.

That’s why I built another guide (inspired by the Board Room Translation Guide I shared in entry 18) focused on helping you translate your day-to-day into the language your VP or CMO will understand.

It helps entry-level and junior marketers share their work in a way that lands with leadership. That means:

• Don’t just say what you did

• Say what it’s contributing to

• Use real metrics to back it up

Here are a few examples from the guide:

🚫 Don’t say: “I scheduled 10 social posts this week.”
✅ Say: “We’re reinforcing our latest campaign with organic posts—3 are already driving high engagement.”
📊 Follow-up metrics: Engagement Rate, Clicks, Impressions

🚫 Don’t say: “I helped with the webinar.”
✅ Say: “I handled logistics and built the follow-up to push attendees into pipeline.”
📊 Follow-up metrics: Attendee Count, Follow-up CTR, Pipeline Contribution

🚫 Don’t say: “I wrote a blog post.”
✅ Say: “I wrote a post addressing a common objection—it’s now ranking on Google.”
📊 Follow-up metrics: Search Ranking, Page Views, Time on Page

🚫 Don’t say: “I cleaned up the database.”
✅ Say: “I removed 4,000 duplicates to improve deliverability and list targeting for Q2.”
📊 Follow-up metrics: Bounce Rate, Deliverability, Segment Health

The point isn’t to oversell or inflate your work. It’s to:

1. Communicate outcomes

2. Show alignment to team goals

3. Develop executive awareness early in your career

I compiled a spreadsheet with 25+ translations to help junior marketers sound more like future leaders. Check it out.

On My First 30 Days as the CMO at Docebo: What I’ve Learned

Starting something new always comes with a mix of familiarity and discovery. You bring lessons from past teams, but you show up with your ears open, ready to learn.

It’s been 30 days since I joined Docebo as CMO. While some things feel familiar—smart people, fast-moving priorities, a product with real momentum—there’s also a lot that’s new. New challenges. New customer stories. A new category that’s being reshaped in real time.

Here’s what I’ve learned so far—and what I think other marketers might take from it too:

1. The market sees the shift and believes in it.

Docebo is evolving from LMS vendor to AI-first learning platform. That’s not just internal optimism. It’s showing up in analyst reports, partner conversations, and customer deals. 

You know it's working when your narrative shows up without you in the room. The key is to audit everything from LinkedIn to sales decks to analyst notes and reinforce the message until it sticks everywhere.

2. Leadership belief fuels velocity

Having a CEO who’s all-in on the mission and the product changes everything. Alessio isn’t just supportive—he’s deeply aligned with where we’re going and why it matters. That kind of leadership creates clarity, speed, and confidence. 

CMOs need that alignment early—syncing often, aligning on narrative, and building a shared lens that cascades through the org.

3. Inspire (our user conference) isn’t just an event, it’s a strategic asset

Inspire 2025 proved that a well-run customer event can do more than generate pipeline. It can shape perception, activate internal pride, and accelerate momentum. We saw it happen in real time. 

Marketers should treat events like product launches: build pre-launch hype, overdeliver in the moment, and turn the outcomes into content, case studies, and campaigns for the next six months.

4. The product wins in enterprise, and it’s expanding

Our strongest customers aren’t just using Docebo, they’re expanding with us. We’re solving big problems in complex orgs, especially customer and partner education. 

That kind of validation has to shape the story you tell. Before you write a positioning doc, shadow a customer call. See the product through their eyes.

5. AI is a differentiator but it needs translation

We have a bold AI roadmap—Creator, Harmony, Virtual Coaching—and customers are genuinely excited. But like most AI, the leap from “cool demo” to “clear value” is where marketing earns its keep. 

You can’t just promote features; you have to frame outcomes. Every capability should contain a story about time saved, pain avoided, or revenue unlocked.

6. Partners could be a force multiplier

We’ve got strong partner foundations—AWS, Deloitte, OpenSesame—but the opportunity is still largely untapped. Partner marketing has to go beyond logos and co-branding.

It’s a GTM strategy. Assign ownership, build joint campaigns, and make partner success part of your team’s metrics.

7. Great brands evolve alongside the business

As the product grows more sophisticated and the market shifts, the brand has to move with it—not in response to a problem, but to stay ahead of perception. At Docebo, we have a strong foundation. 

But like any ambitious company, maintaining brand freshness means revisiting the story, tone, and design regularly to reflect who we’re becoming—not just who we’ve been. A great brand isn’t static—it’s a lens that sharpens over time.

8. Revenue marketing and BDRs are in sync

One of the strongest parts of the business is how aligned our demand gen and outbound teams are—especially in mid-market. This isn’t accidental. It results from shared goals, tight feedback loops, and mutual trust. Alignment isn’t a slide in a strategy deck. It’s a daily habit. Reward it.

9. The seeds of thought leadership are strong

Between Brandon Carson, a sharp content team, and a company leaning into AI, the ingredients for real thought leadership are here. But it won’t happen by accident. Docebo is already a market leader—we have the insight, the customer stories, and the data to back it up.

Now it’s about putting structure behind it. Pick a few big themes. Assign ownership. Commit to a cadence. Consistency is what separates insight from noise—and leaders from participants.

10. Resilient teams move the needle

The Docebo marketing team has been through change (new leadership, shifting market, evolving structures) but they’ve kept moving. They’ve delivered major events, launched campaigns, supported the entire company, and kept the brand present. That kind of grit doesn’t show up on a slide, but it shows up in the work.

Resilience isn’t just endurance—it’s belief in the mission, even when the direction changes. And this team believes.

And ultimately, the team is what makes it all worth it. Joining Docebo is a new adventure. And while I’ve been part of fast-growing companies and talented teams before, I didn’t walk in assuming the playbook would carry over.

Instead, I came to listen. To learn. And to help shape what comes next.

So far? The signal is strong. The opportunity is big. And the people? They’re the best part.