The Letter From The CEO

Breaking down the leader-led marketing move you almost certainly haven't tried yet (but probably should)

B2B marketers have a lot of tools at their disposal, but there's one most don’t even think about putting to work: A simple, direct letter from their CEO.

Which is a little weird. Because people want to know what the person leading your company is thinking, seeing, and feeling.

Here’s how you can give the people what they want, direct from the C-suite, and including a few of my favorite Letter From The CEO examples you can steal from.

Why People Read These

The CEO seat might be the loneliest job in business. It’s also one of the most opaque. CEOs are paid to connect dots that others might not ever get the chance to even see. They aren’t just making calls on products or campaigns; they’re constantly assessing risk, opportunity, and alignment across an entire company.

That stuff is interesting. And most marketing content never even touches it. Instead, we get the predictable “we’re great” sales pitch or a generic press release that reads like a mad lib.

Is all that necessary? Sure. You’ve got to cover your bases.

But is it fun to read? Is it inspiring? Uh, no. No it is not.

What’s missing is the voice that brings all these moving parts together from a vantage point of real, informed, executive-level accountability. When a CEO steps in to share their thinking—not just on the what, but on the why and how—they offer a perspective that cuts through the noise. It’s a reset button. It’s a chance to hear how someone handpicked to lead a business and a team is navigating a multi-faceted game as it unfolds.

And it’s about something deeper: how they balance the visible strategic moves with the internal reflections that shape their decisions.

The Inner and Outer Game

In the leadership development course we use inside our portfolio, we dive deep into the concept of the inner vs. outer game. This concept is all about balancing the internal focus, mindfulness, and energy (the inner game) with the external, “outer game” demands of business—strategy, customers, products, and teams. Mastering leadership is learning to juggle both games: Staying grounded while executing in the real world.

A great CEO letter is balanced in a similar way. It’s not a bland market update or a disguised internal memo. It shows how the CEO is balancing the "outer game"—market strategy, big moves, trends—with the "inner game"—the tensions they’re feeling, the reflections on how decisions impact company culture, and the stories that make those reflections real.

When a CEO opens up in this way—sharing their market view paired with what’s going on behind the scenes—that's when people lean in. It’s not just another update; it’s proof that your company has something to say and something to teach. It’s also proof that your CEO isn’t stuck in an office bubble. They’re tuned in, actively leading, and offering real insight into what’s shaping the company’s path, including the obstacles and surprises they’re encountering along the way.

Example #1: Fleet.io

Take CEO Jon Meachin’s post-show recap for Fleet.io as an example. After a major tradeshow, he didn't just stop at saying why his company is great or why you should care about the products they showcased. Instead, Jon went deeper—sharing unique perspectives, stories from the event, and highlighting individual team members' contributions. It’s the kind of stance-taking angle that feels genuinely authentic—something only Jon and Fleet.io could have written. This approach balances the outer game (market insights and strategic takeaways) with the inner game (reflecting on the company’s culture, direction, and the people who make it tick). The result? A piece that feels both insightful and personal, cutting through the typical post-even content clutter.

Example #2: DealerBuilt

Then there’s CEO Max Longin’s letter after the automotive industry’s biggest trade show, NADA. Max took the time to unpack a common industry buzzword: “Consolidation.” But he didn’t just use it as another piece of jargon to impress. He broke it down with real-world examples and a market-informed point of view, explaining what consolidation means not just for businesses, but for individual employees. This “let me tell you how I see it” tone stands out in a sea of content that rarely digs deeper than surface-level SEO stuff. Max’s letter isn’t just a recap; it’s an educational piece. It demonstrates that he’s not just repeating what everyone else is saying. He’s taking a stand, explaining the thinking behind it, and offering some genuine insights and opinions.

Example #3: Untoxicated

I’ll get my bias out there upfront: Untoxicated is my wife’s startup. Annie and her co-founder set out to build a truly allergen-free sensitive skincare brand after realizing most “sensitive skin” brands still manage to sneak in allergens, irritants, fragrances, parabens, and a bunch of other junk that can wreak havoc on anyone with sensitive skin—a market that, by the way, includes more than half of the U.S. population.

Check out Annie’s Ideal Investor Profile. A creative twist on the concept of the ideal customer profile, she doesn’t just pitch Untoxicated - she makes it clear who they want in their fundraising corner and why. It’s a great example of playing the "outer game" (attracting the right kind of investors) while keeping the "inner game" (staying true to their values) front and center.

Then there’s her “Clean” post, taking aim at what “clean” should actually mean in the world of skincare. Just like Max’s take on “Consolidation,” Annie takes a scalpel to an overused piece of industry jargon, breaks it down, and calls BS where it’s needed. It’s bold, it’s direct, and it’s a perfect example of how you cut through the noise to tell your story without being too sales-y.

Timing is Everything

Great, so now you have some guidelines on what to write about in a letter from your CEO. But when should you write one?

Here’s my take. The CEO letter works best when it’s tied to a “big deal” event. Think tradeshows, product launches, your first few months after joining as a new CEO, or major M&A announcements. These moments are ripe for reflection. They’re the times when people—whether they’re customers, partners, or employees—are actively seeking clarity. They want someone to break it down for them in plain language: “Here’s what’s going on, and here’s what you should pay attention to.” But a word of caution, the half-lives of these reflective periods are short. So start your planning process before the event. This will not only help you get it our more quickly, it’ll arm your CEO with a mental outline to fill in while they’re experiencing what they’re going to write about.

There’s a reason why this kind of timing works so well. We are clarity-seeking creatures. When something big happens, we immediately start trying to make sense of it all. The CEO, the position that Twitter founder Jack Dorsey once referred to as “the editor-in-chief of the company”, is a uniquely-qualified person to play that sense-making role. They can connect the dots between high-level strategy and the everyday realities of the market. They have a trusted voice that can credible say, “Here’s what matters, and here’s why.”

This trusted voice, channeled into a well-structured letter, can be just as powerful in more “inside baseball” situations. Big organizational changes, for instance. My favorite example?

Patrick Collison

’s letter to Stripe employees addressing the company’s layoffs. This CEO letter is a masterclass in transparency, leading with honesty, acknowledging the tensions that Patrick was feeling while making a tough decision, and laying out a clear vision for the future that supported his call. Reading it, you can’t help but feel comforted by the clarity. “Ok, this sucks, but I get it,” I found myself saying. Provided it’s coming from an authentic place, this is exactly the kind of reaction you’re going for as the leader of a company going through tough times.

For The Skeptics

Now, some of you out there might be thinking, “We already send newsletters and product updates. How is this different?” Well, try this. Read your last newsletter or product release announcement aloud. As you’re reading, ask yourself this: Do you sound like a person or a company? If you’re like most B2B businesses, it’s the latter. And simply injecting a more human voice into your marketing every once in a while is a great way to keep yourself from being tuned out in a business world that’s only getting noisier.

The other reason this is worth trying: It’s an easy way to send a powerful signal of trust. You can claim all day that you’re innovative, customer-centric, or that you have a great culture. Write all the copy you want proclaiming those points. But in a CEO letter, you get a chance to show it. By using real stories, reflections, and evidence, you turn those claims from mere talk into something more believable. Something you can stand behind. Something you can be a little, I don’t know, proud of.

So the next time your company hits a big milestone—whether it’s a tradeshow, a new product launch, or a major strategic move—don’t miss your chance.

Let your CEO do the talking. You might be surprised by how many people want to listen.