Don Draper Doesn’t Work Here Anymore

A CEO once told me, "I want you to pretend you're Don Draper and give me a pitch of what we should be doing."

It was intended to be inspirational, but here's the thing: I'm not Don Draper. And Don Draper-style marketing wasn't what the company needed.

As Draper himself said, "If you don't like what's being said, change the conversation." Changing the conversation is exactly what today's B2B startups need to do when it comes to marketing.

Marketing Isn't One-Size-Fits-All

What’s the most common mistake I see growth-stage CEOs make? 

Hiring "a marketer" and expecting them to do it all: brand, content, demand gen, product messaging, customer advocacy, digital ads, the website, and maybe even a trade show.

It's the startup version of the unicorn hunt. And it almost always ends the same way: misaligned expectations, underwhelming results, and another search 10 months later.

Marketing isn't one job. It’s not even one department. It's a system of highly specialized disciplines, each with its own tools, mindset, and success metrics. And while they work best together, they are not interchangeable.

Here's how the work typically breaks down:

• Brand marketing defines who you are, what you stand for, and how you're perceived in the market. It is your identity—visible across your website, messaging, and market presence.

• Demand generation drives pipeline and revenue by converting interest into action. These programs fill the top of your funnel and keep it moving.

• Product marketing translates features into value and helps sales teams and customers understand why your product matters. It connects the dots between your customer’s pain and your offering as a solution.

• Customer marketing focuses on adoption, retention, expansion, and loyalty, fueling long-term revenue growth through satisfied, engaged customers.

What You Think You're Hiring vs. What You Actually Need

My Don Draper moment? A classic case of misalignment.

The CEO wanted brand storytelling and creative vision. But the company actually needed a builder. Someone to create a growth engine, align marketing with sales, and deliver leads that convert into the pipeline. 

I was built for the latter. I’m technical, systems focused, and results driven. But it wasn't the right match for the CEO’s vision. One year later, I was out.

This isn’t a one-off story. Mismatches happen all the time.  Not because the marketer isn’t capable, but because the company didn’t clearly define what kind of marketing leadership it needed at that stage.

If your mental model of a marketer still looks like Mad Men, it’s time for an upgrade.

Modern marketing isn’t a one-person show, it’s an ecosystem of specialists. Brand, demand gen, product, customer—each one brings different skills. And while a single hire might be able to check one or two of those boxes, no one person can deliver across the entire spectrum well.

Here is the rub: Most companies can’t afford to build a full in-house team. And hiring just one marketer and expecting them to wear five hats is a setup for frustration, on both sides.

That’s why structure matters more than headcount. 

The best play: Bring in a strategic leader who can assess what to build now, what to plan for later, and how to work with you to prioritize the right investments at the right time. This is where fractional leadership becomes a force multiplier.

Why a Fractional CMO Makes More Sense

When you're in scale mode, every hire matters. You don't need to commit to a $300K/year CMO to get strategic clarity. You need a scrappy, seasoned leader who can:

• Assess your stage and architect a plan that aligns with revenue goals

• Identify gaps across your current team, tech stack, processes, and messaging

• Prioritize investments across brand, demand, product, and customer marketing

• Build foundational systems that scale as you do

• Help you hire smarter when you're ready to build a full team

That's the power of a fractional marketing leader: executive-level expertise and decision-making power without the full-time overhead. And because they come with a whole team of additional professionals, you avoid hiring a specialist when you need a strategist, or vice versa.

Here’s what sets great fractional CMOs apart:

• They’ve learned to thrive in lean environments

• They bring systems thinking and hands-on execution

• They come with a trusted bench of specialists, freelancers, boutique partners, and proven collaborators

You get executive-level horsepower and a whole team for execution—all without the full-time overhead. You skip the mis-hires. And you start building marketing that actually drives growth.

Curious how a fractional CMO can help your startup avoid costly mis-hires and build a marketing foundation that actually drives growth?

Here’s what that looks like »

Ready to hire smarter, not bigger?

Let’s talk about hiring a fractional CMO »