What B2B startups get wrong (and right) when hiring marketing leadership

"And out of the wilderness rode the Renaissance Man atop his faithful unicorn, destined for the Goldilocks pass..."

It’s an old story, and one that tends to repeat itself: early-stage companies often view marketing as merely the “Promotion” part of the Four Ps we learned about in university—at worst, a “coloring-in” department responsible for pretty designs and catchy taglines. At best, it’s the team charged with the hyper-measured and often thankless task of managing endless Google and LinkedIn ads, day after day.

This is an outdated perspective. As product- and sales-focused leadership quickly learns, marketing is neither a passive function nor one that should be pigeonholed into a small mandate. But it’s a lesson that tends to arrive later than it should, usually after much trial, error and exclamations of “Wow, I never realized Marketing was so broad”. 

Here are a few things founders should consider to hire marketing more effective:

The Common Path vs. Serial Founders

Here’s how it often goes: “Let’s bring in a junior marketer to execute the work. We’ll give them direction; they can figure out the rest.” Sound familiar? This is the route many first-time founders take. It’s also why so many young marketers find themselves crowned “Marketing Lead” or “Head of Marketing” long before they've earned it. And while a few rise to the occasion, many don’t.

When these young marketers are left to figure things out with little direction from non-marketing managers, it’s like tossing someone into the wilderness with a compass, but no map. Sure, they might eventually find their way out, but the time lost and the frustration it causes can be overwhelming.

Serial founders? They’re often wiser. They know better than to leave marketing to chance. They bring in a seasoned marketing leader, augment them with junior staff, and foster an environment where execution meets experience. But let’s be real, how easy is it to find the right fit?

Would Goldilocks Date a Renaissance (Wo)Man?

We all dream of hiring that marketer who sits right in the Goldilocks zone: not too inexperienced, not too seasoned. They’re ambitious, talented, and capable of handling everything from demand generation to content creation, branding, PR, and sales/marketing alignment.

But, let’s face it—that perfect marketer is rare. In fact, the pool of candidates who can masterfully juggle all aspects of modern marketing is incredibly small. Even smaller when you factor in the budget constraints of early-stage companies. Instead of chasing unicorns, maybe the answer lies in creating your own. Enter the “Unicorn Farmer”—also known as the Fractional CMO, but I might be a little biased there.

When Do Businesses Realize They Need Marketing Leadership?

When marketing can’t keep up—that’s the tipping point. Either the business growth is hitting a wall, or marketing simply isn’t delivering the numbers to match the company's needs. This happens when a company maxes out individual channels, and further excellence in digital or content marketing won’t move the needle unless you dramatically increase spend. Or maybe they’ve neglected brand-building altogether, focusing solely on performance marketing.

At this juncture, companies are faced with a choice: do they hire more specialists, potentially drowning themselves in overhead? Or do they promote internally, risking that the increased responsibility might sink the performance of a rising star? External agencies can provide quick wins, but managing all those moving parts can overwhelm whichever non-Marketing executive has the task alongside their supposed focus of product or operations.

The Danger of Hiring "Too-Experienced"

Maybe you have the budget to solve your marketing woes and decide to go big—hire someone very senior from a tech giant, where they’ll “teach us how to do it the [insert tech giant here] way.” But that might come with baggage. Someone who’s used to working in a thriving, well-funded environment may not thrive with your limited runway or in your cash-strapped, bootstrapped startup.

Similarly, hiring someone with 25+ years of experience could work in sales, where extensive networks are invaluable. But when it comes to marketing, those with deep boardroom experience often struggle to get their hands dirty. And, after years of navigating corporate politics, some may have forgotten how.

So, Who Do You Need?

You need someone equipped on three fronts: strategy, training, and execution. It’s a balancing act between being in the trenches and leading from the front, all while keeping the big picture in mind and driving growth forward. They’ll likely need to handle:

• Strategy: The leader needs to communicate up and down the chain, aligning the team’s efforts with the company’s vision while getting buy-in from both sides of the table. The CEO has the vision; the marketing team has the channel expertise. The leader sits at the intersection, orchestrating it all.

• Training: A great marketing leader helps unlock the potential of the existing team. This goes beyond providing guidance—it’s about giving them the right direction, so they don’t waste time on the wrong tasks. The leader spots patterns, steers the team toward opportunities, and offers shortcuts to knowledge that only come from experience.

• Doing: Lastly, a marketing leader must remain close to their domain. They should still be involved in some of the work, whether it’s writing content, setting up campaigns, or working on messaging and branding. In small organizations, the leader must still “build the plane while it’s in the air”—just like everyone else.

Conclusion: The Effort Multiplier

Great marketing leadership isn’t about staying in the boardroom or letting the juniors figure it out on their own. It’s about being a coach-player—strategizing, mentoring, and getting into the action when needed. When you find the leader who can do all three, that’s when you’ll see the team—and the company—reach its full potential.

Image generated with Flux AI