Letter to the future CMO
What I'd want to know before I got there
There’s a moment every B2B marketer knows.
You’re sitting in a quarterly business review. Sales leadership stands up first. They missed the revenue target again. The team was working hard, but the results just weren’t there.
Then marketing leadership stands up. Another strong quarter. Surpassed the MQL target yet again.
And nobody in that room says a damn word. Nobody questions how both of those things could be true at the same time. They just move on.
I sat in that room early in my career and it’s something I’ve never been able to forget.
15 years later, I’ve done something about this. I built Affect - the platform I’ve always wished for as a marketer.
Affect is for the marketers who have sat in a room where marketing celebrated hitting its targets while the business missed revenue - and felt sick about it.
The marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself.
The marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.
The waitlist is open today. It would mean a lot to have you on it 🙏
My dear future CMO,
This final letter is different.
The first four I wrote to you came from a place of having lived it - the mistakes, the lessons, + the moments where I wish someone had handed me letters like these. But this letter is written from a different vantage point as I haven’t sat in this seat. I’ve watched enough people who have been there to know what I’d want to be thinking about before I got there.
So take this one for what it is - observations from someone still on their way up, written down before the moment arrives.
The first thing that will catch you off guard is that the job is less about marketing than you think.
At every level before this one, your value was tied to your ability to understand + execute marketing. At the CMO level, what actually matters is your ability to translate marketing into language the business cares about. Things like impressions, brand lift, and keyword clusters don’t mean anything outside of your marketing team.
The table you’re sitting at now is discussing revenue, margins, market position, + advancing your competitive advantage. If you can’t make that transition fluently + quickly, you’ll have a short tenure fighting for budget + credibility instead of actually leading.
And then there’s the fun part that makes it even harder - you’re almost certainly the most misunderstood executive in the room. The CFO has their financial model + the CRO has their revenue number, two very quantitative measures with binary over/underperforming metrics. The CMO has a qualitative story about why the market sees you the way it does, what it’ll take to change that, + some hypothetical models for what the outcome could look like.
Getting the room to receive that story as strategy rather than opinion is work that never stops. You’ll educate as much as you execute. Then you’ll re-educate again in a few quarters when something is “off” and the lesson has been forgotten because it never showed up cleanly in any report. This is the job now. You need to be able to market internally just as well, if not better, than you can market externally.
A second lesson: your relationships will determine everything.
Your relationship with the CEO is the foundation your entire role is built on - more than your strategy, your team, + the quality of your work. If the CEO doesn’t understand what you’re building + why it’ll work, you’ll always be one bad quarter away from having “the conversation” that no CMO wants to have. Invest in this relationship like it’s the most important project on your list.
Then there’s a second relationship most CMOs underestimate - the one with the CFO. These two functions have historically talked past each other - marketing speaks in qualitative measures, finance speaks in quantitative measures. The CMOs who figure out how to close that gap early are the ones who end up with more budget, more trust, + more room to make the big bets. You are the person who will determine if marketing is viewed as an expense or an investment.
And for your final lesson: you’re going to make a lot of decisions in this seat. Hundreds, if not thousands, of calls across strategy, budget, people, execution, messaging, positioning, + much more. But when you + others look back on your tenure, you’ll likely be defined by only one or two of those decisions: that one big swing that really worked, and then the one bet that completely flopped. It won’t be the sum of everything you did. That’s the strange one to sit with, but it’s worth thinking about now before you get there. It will inform how seriously you treat the biggest calls + how much conviction you’re willing to bring to them.
You’ll be sitting with a lot of things alone at this level. There’s nobody above you in marketing inside the company to learn from or bounce ideas around with anymore. The peers who used to be your sounding board are now your direct reports. You’ll have to be the person in the room who says the hard thing nobody else will say - whether it’s about the strategy, the market, what’s not working, or who isn’t pulling their weight. This is a burden that is yours alone. It comes with the seat.
You’ll skin your knees on a few of these before they click. That’s ok, that’s how this works. The ones you learn the hard way will stick the longest.
Ever faithfully yours,
Sam
P.S. If this helped with where you’re at now, or would have when you were at this stage, share this with someone else you know who would benefit from it.
Sponsor: YOYABA
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On May 7th, Oliver Kuttruff (Senior SEO Consultant at YOYABA) and Crystal Carter (Head of AI Search & SEO Communications at Wix) are breaking down what an agent-ready website actually looks like in practice:
What WebMCP is, what it isn't, and how to pick between Declarative and Imperative API approaches
Which strategies are production-ready today and which "hacks" you can safely ignore
How SEO is shifting from ranking pages to enabling agent actions
If you're overwhelmed by the AI agent noise and want clarity on what's actually worth implementing, you won’t want to miss this. May 7th, 2026 from 9:30-11a EST / 2:30-4p BST.
Editor’s note: This is letter 5 of 5 in a series of letters to a marketer at a major inflection point in their career - the letters I wish I had at those times. If you want to start at the beginning, here they are:
To the first-year marketer
To the first-time manager
To the first-time director
To the first-time VP
*AI disclaimer: stealing this from Ashley Lewin. It’s important to be transparent when it comes to AI usage in marketing. You all (hopefully) trust me + let me drop into your inbox each week, and I don’t want you to think I take that for granted.
I used AI for this week’s newsletter (and the others in this series) to help structure the writing in a way that allows me to be shorter, more direct, + have more of a “lessons + love from someone who’s been there” dynamic to it. I’m sure you picked up on that in the writing style here. My ideas, but in a slightly different style + delivery than normal in an effort to make this series more impactful.