I made it a point this year to only write for Revenue Diaries when I felt "led," which is why I haven't posted in a couple of weeks. The parts work I've been doing with Michael Brabant has given me a lot of clarity on where to place my energy on any given day. Some days I want to write and share, and other days I’d rather focus on other aspects of life.

And this weekend? I wanted to write. So, I’ve got two things for you this week: a new podcast I’m launching called Head Trash and the first five lessons I’ve learned as a marketing leader over the last 15 years. 

First things first, and then on to the marketing stuff. 

I've dealt with low self-esteem and imposter syndrome my entire life. Doesn't matter how successful I get on paper, the voices don't go anywhere. I call it head trash. The small, chattering nonsense in your head telling you what to do, why to do it, and exactly how you're going to screw it up.

So, starting next month, I’m launching a new podcast/conversation with my friends called Head Trash, a Revenue Diaries Joint (shoutout to the GOAT, Spike Lee). My plan is to have 15 to 20 minutes with one guest about how they wrestle with the voices in their own head. My friends at Share Your Genius are producing it, same team that puts out two other shows for us at Docebo, 

If you want to come on and talk about your own head trash, just reply to this email. I read every one of them, and I'd genuinely love to hear how you're dealing with yours.

Alright, onto the marketing stuff.

Last week I taught the first session of Pavilion's CMO School, ninety minutes on the twenty lessons I've picked up over fifteen years of running marketing teams at high-growth software companies. It's a lot. I mean that literally; the list is genuinely exhausting, so I'm not going to dump all twenty on you today. I'm covering the first five here (Revenue & Pipeline), and I'll get through the rest over the next few weeks. If you want the full ninety minutes before then, ask me about the CMO School cohort and I'll point you the right way.

Let’s do it. 

♥️ kyle

20 Lessons from 15 Years of Marketing Leadership

20 Lessons from 15 Years as a Marketing Leader ie: How to Not Get Fired 

I’m pulling this content straight from a 90-minute talk I gave to Pavilion’s CMO School last week around the LARGE amount of lessons I’ve learned over 15 years of running marketing teams for high-growth software companies. 

Here's the full list: 

Revenue & Pipeline

• Own a Number Tied to Revenue

• Report the Number Weekly

• Monthly Pipeline Council

• The Revenue Handbook

• BFF Your CRO

Executive Comms 

• Red Team Everything 

• Translate Marketing Into Exec Language 

• Make the Invisible Work Visible

Team & Culture 

• Lead with Clarity 

• Stop Asking Permission to Do Your Job 

• Cultivate & Protect Good Taste 

• Co-Own Enablement 

• Give Them Space to Change

Budget & Brand 

• The 80/20 Rule
  When to Rebrand 

• You Must Measure Brand 

• Build a Care Narrative & Manifesto

Leadership & Career 

• AI Adoption is Mandatory 

• Hire a PMM & a Great Designer Sooner 

• Know When to Leave

It’s pretty exhausting to read because it’s A LOT. I’m going to cover the first five in today’s entry and cover the rest in the next couple of weeks. Take your time reading and if you want the full version, don’t hesitate to ask about the CMO School. 

Let’s get into it. 

1. Own a Number Tied to Revenue (Pipeline)

I opened with a quote I've been using since 2013, from a guy named David Wamsley who ran digital for Marks and Spencer. 

"We must move from numbers keeping score to numbers that drive better actions."

I've used that line every year for over a decade because it best explained what it meant to be a “revenue” marketer. 

As a marketing leader, you do not have a seat at the proverbial table unless what you do ties to dollars. And how you communicate matters almost as much as the number itself. There are zero board members that care about “growing leads 45% year/year. They care that those leads converted and drove X millions in pipeline and eventually… revenue. 

Somebody asked me a question after briefing opining on why brand was swinging back around as “important” as AI makes the revenue role a little less intense. 

“What happens to demand marketers how that the pendulum has swung back to brand?” 

My answer was a little rough because it was real time but here’s the gist: they still exist, because it's still important, but I've had to get more aggressive about owning the brand and storytelling conversation too. Because if you don't, guess who takes it from you? Product and sales. And product and sales are good at what they do, but they'll drag you into a feature war that's boring as hell for everyone involved.

Owning the pipeline and revenue number is how I was promoted into my first CMO role at Lessonly. Nobody was truly owning the top-of-the-funnel attribution model or the how the assumptions were tied to the financial model. 

Like many places, finance was building the model and handing it down to the team. That’s 100$ backwards. You want to build it with finance, not get it handed to you. And once you own/help build the model, it makes sense to bonus the team on it. 

In most of my teams after 2017, I’ve bonused the team on pipeline and revenue goals. 

We’ve taken it one step further at Docebo with product marketing. They co-own the pipeline number with product managers for the product they support. Creative and brand still get tied to the overall pipeline, because we want everything moving in the same direction, no matter what. 

2. Report on the Number Weekly

Once you own the number, it’s important the you report on it. At the end of the week at Docebo, every pipeline owner (inbound, outbound, partnerships) updates a shared Slack canvas that covers the following: 

Bottom line

• On track or off track?

• What are you pacing to vs. plan?

If something is off track

• What’s broken or at risk?

• What are you doing about it?

• What should we expect to change over the next 1–2 weeks?

And there are a few rules to follow: 

• All pipeline numbers must be updated in the shared dashboard by RevOps

• Updates are required every week, even if numbers are flat.

• If you own a row of pipeline, you own the update.

After the team updates the numbers, every Monday or Tuesday, myself, our CRO, and VP of Rev Ops review the canvas update. If something’s off track we review what’s broken, what are we doing about it, what should change in the next week or two. 

One person from the class pushed back a little bit asking “Doesn’t weekly sometimes feel redundant when the numbers barley move? Especially if you have longer sales cycles?” 

I told her I don't care about redundancy. It's supposed to feel repetitive, because repetition is what builds the muscle. The alternative (which I don’t want to do) is chasing people down at the end of the quarter trying to reconstruct what happened, and that's a much worse way to spend your time. If you own a row of pipeline, you own the update, even if the update is "still flat, still fine."

The golden rule underneath all of it: never surprise your CEO. Good news or bad. I gave the group an example. Say your enterprise unit volume starts dropping week over week while your dollar number holds steady. You flag it early, even without a fix yet. You come back a week later with what you found. By the time it shows up as a board question, your CEO already knows the story and isn't caught flat-footed.

And then the question was raised, “Shouldn’t you only go to your boss once you have a solution, or the moment you spot the issue?” I told them even a half-formed direction beats silence, believe me. I’ve tried silence. If you wait two weeks for the perfect answer, you've just given the surprise more time to grow and fester. "Here's the issue, here's what we're thinking" is already miles ahead of saying nothing.

And the way you avoid all surprises across the revenue/executive team? 

3. Start a Monthly Pipeline Council

All the weekly updates discussed previously are async unless a meeting is absolutely needed.   The pipeline council is the important meeting, and it can happen monthly or twice a quarter, completely up to you. People in the room: CEO, CFO, CMO, CRO, and the VPs of sales, RevOps, and revenue marketing in the room. Otherwise known as… leadership and the stakeholders/channel owners.

Don’t think you just drop into the meeting and talk about dashboards. It’s important that you add some context to the discussion. And as boring as it sounds, I highly encourage you to use a pipeline memo and it has four sections: 

1. An executive overview covering what's working and what needs fixed. 

2. Pipeline attainment broken out by channel, segment, and industry. 

3. Pipeline coverage for the sales team with two future quarters covered

4. Pipeline goals + next quarter forecast/goal by segment, unit and dollar

And this sh*t used to take a ton of hours, now it only takes a couple of hours. All those weekly Slack canvases from every pipeline owner feeds directly into Claude, which builds a first draft of the memo. My team gets in, edits it, sharpens the story, and then it goes to the exec team. The constant weekly updating is what makes this possible because NOBODY wants to scramble at the end of the quarter trying to reconstruct what happened for the board meeting.

4. Spin Up a Revenue Handbook

I haven’t actually done this at Lessonly and Docebo is a little large for it, but if you are at a startup, this is HUGE. It covers all things go-to-market. Follow-up SLAs for inbound leads, how fast an AE has to move something into an opportunity, territory rules, account ownership, parent and child account logic. Document it and get it signed, literally, I've sent this out as a DocuSign to the entire team… which is hilarious. :)

Why is this doc so important other than alignment? Arbitration. As you grown, you will end up in a fight between a BDR and an AE over who gets credit and who gets comped. If it's written down, you point to the doc and move on. If it's not… well… it’s annoying as hell. 

You don’t need to recreate it. Click here and make a copy! 

5. BFF Your CRO

I showed a photo of me and Mark Kosoglow, and a quote from our VP of RevOps: "I'm not sure how to behave when the CRO and CMO actually like each other and work together." I laugh every time I read that, because it shouldn't be rare, but it is.

When you're in a board meeting or leadership team meeting, does anyone care about the brand campaign that drove five customers to an event? No. They care about revenue. If you're hitting your pipeline number, nobody questions your brand spend. If you miss it, that same brand spend becomes the first thing on the chopping block, and your CRO is either your ally in that room or your problem.

I'm lucky. Mark built Outreach from zero to a hundred million before he came to Docebo, and he and I talk pipeline coverage daily. We definitely live in a world where we both believe that marketings goal is so important, and I quote the wonderful Udi from Gong: 

“Marketing’s job is to make sales easier.” 

And the only way you can achieve that, is to have a good working relationship with your sales counterpart. 

Alright. That’s five down, fifteen to go. Now I’m very lucky to have beautiful weather tonight in Indianapolis. I’m going to spend the rest of the fleeting Sunday evening hanging out with the family.

Next week I'll get into red teaming your board deck, translating marketing speak into something a CFO actually understands, and why visibility isn't bragging… along with much, much, much, much more.