Critical Marketing Mistakes by B2B Tech Founders & CEOs

Here's the thing about marketing problems: they're almost never problems that more tactical marketing activity will solve.

I've spent more than two decades in B2B marketing—inside companies, advising founders, helping CEOs figure out why growth has stalled. And I keep seeing the same patterns. Pipeline is weak, so they run more campaigns. Leads aren't converting, so they try new channels. Messaging isn't landing, so they rewrite the website. Yet again.

But the real issue is usually upstream—in the clarity and strategy work that should come before tactics. Who are you for? What makes you different? Why should anyone care? Get that wrong, and no amount of activity will fix it. (Trust me. I've watched people try.)

Most founders I talk to are smart, capable people. They've built something real. They understand their product inside and out. But when it comes to marketing, they're operating with a set of assumptions that quietly sabotage their efforts.

Here are the mistakes I keep seeing—grouped into three categories. Some will sting. That's probably a sign they're worth paying attention to.

1. Strategic and Foundational Misalignment

These are the upstream issues. The stuff that, if you get it wrong, makes everything downstream harder than it needs to be.

Lack of Strategy and Focus

You're running Google ads. Hired a cold-outreach firm. Posting on LinkedIn. Maybe sponsoring an event or two. But there's no unifying strategy connecting any of it. Just activity. Sound familiar?

Here's what that looks like from the outside: scattered. And here's what it produces: diluted results and burned budget.

Marketing without strategy is just expensive noise. And then you'll wonder why 'marketing doesn't work.'

Misunderstanding Scope (The 'Arts and Crafts Department')

Many founders view marketing as the team that makes things look pretty—websites, slide decks, social posts. Oh, and swag. There has to be swag. Tactical stuff.

But real MARKETing (hint's in the name) is much broader: customer and market research, segmentation and targeting, positioning, go-to-market strategy, brand building. It's the work that connects what you sell to who actually cares.

When marketing gets reduced to 'Arts and Crafts,' you lose the strategic engine. Don't be surprised when your 'marketing team' can't move the needle on revenue. They're not set up (and depending on who you hired, may not have the skills) to think that way.

"We'll Do Marketing When the Product is Ready"

This one's everywhere. Founders treat marketing as something that happens after the product is ready for release.

But if you wait until then to start marketing, you have no one ready to buy. You're spending dollars with no revenue coming in. Know how that ends? The foundational work—positioning, messaging, go-to-market strategy, target audience definition—should happen while you're building the product, not after.

Done right, this work also produces a product customers actually want. Funny how that works.

Product vs. Problem Focus

Tech founders love their product. They know every feature, every technical nuance. And they want to tell prospects all about it. (Whether they asked or not.)

The problem? Customers don't care about your features. They care about their problems—and whether you can solve them.

Messaging that leads with features instead of problems lands flat. It's the difference between "Our platform uses AI-powered analytics with real-time dashboards" (who cares?) and "Stop flying blind on pipeline—know what's working before you run out of runway" (that grabs attention).

Poor Positioning

Positioning answers the big questions: Who are you for? What problem do you solve? Why should anyone pick you over the alternatives?

Without clear answers, you blend into the 'sea of sameness.' Your website sounds like everyone else's. Your sales team struggles to articulate why you're different. And prospects mentally file you under 'generic'. And 'generic' doesn't get shortlisted. This is the biggest problem that I see.

Good positioning makes everything easier—sales conversations, marketing messages, even product decisions. Skip it, and you're building on sand.

2. Mismanagement of Resources and Expectations

These are the mistakes that happen when founders hire marketing help but set them up to fail—through misaligned expectations, limited access, or fundamental misunderstandings about what's required.

Assuming Marketing Requires a Big Budget to Start

Founders often delay marketing because they assume it means paid campaigns, agencies, and media spend. "We'll do marketing when we have budget."

But the foundational work—customer and competitive research, positioning, ideal customer profile (ICP) definition, messaging—doesn't require big dollars. It requires time and expertise, not ad budget.

By waiting, you lose months or years of groundwork that would make your eventual spend far more effective. The irony? Companies that delay marketing because of budget end up wasting more money when they finally do invest. They skipped the thinking bit and went straight to the spending bit.

Hiring Junior People for Senior Jobs

You need marketing help, so you hire a Marketing Coordinator or Marketing Manager and expect them to "build marketing from scratch."

Here's the problem: they don't have the experience to develop strategy. They're good at execution—running campaigns, writing content, managing tools—but they've never built a marketing function from zero.

They need guidance, coaching, and strategic direction. Without it, they're set up to fail. And when they do, founders conclude that 'marketing doesn't work for us.' Spoiler: marketing works fine. You just didn't set anyone up to do it properly. That's on you.

Lack of Trust and Micromanagement

This one's especially common with founders who have bootstrapped marketing themselves. They hire a marketing leader but can't let go.

Every decision gets second-guessed. Every recommendation needs "validating." The marketing leader ends up executing the CEO's preconceived ideas (or their niece’s ideas because she’s nailing TikTok) rather than their own strategy.

If you're paying for expertise, let it breathe. Otherwise, you've just bought yourself an expensive order-taker. And when results don't come, you'll have no one to blame but yourself.

Treating Marketing Leaders Like Outsiders

Some CEOs treat marketing like a vendor relationship—excluded from board meetings, kept away from sales data, cut off from the product roadmap. The marketing leader ends up working with half the picture. You're telling them they're not really part of the team. Don't be surprised when they act like it.

To get maximum value, the marketing leader needs a seat at the table and full access to data and stakeholders. This is especially true with fractional or part-time leaders who have limited hours and need full context to be effective.

Unrealistic Timelines and Neglecting Brand Building

Marketing isn't a sprint. Building brand awareness and trust, developing strategy, generating high-quality inbound leads—this takes time.

Brand marketing is especially vulnerable because it's hard to measure and doesn't produce immediate ROI. So founders deprioritize it. "We'll do brand later."

But here's the reality: only a small fraction (as low as 3-5%) of your market is ready to buy at any given moment. Brand building keeps you visible and credible with the majority who aren't ready yet. Neglect it, and when those prospects do enter the market, you're not on their list. You end up starting from scratch with every opportunity. Groundhog Day, but with a smaller budget.

Expecting More Activity to Fix Foundational Problems

Pipeline is weak. Growth has stalled. So the CEO pushes for more marketing activity—more campaigns, more content, more leads. More leads isn't a strategy. It's a wish.

But if the real issue is unclear positioning, fuzzy ideal customers, or weak differentiation, more activity won't help. You're just amplifying a broken message to the wrong audience. Louder isn't better when what you're saying doesn't make sense.

A good marketing leader can diagnose and fix these foundational issues—but only if they're empowered to do strategy work, not just told to "generate more leads."

3. Internal Alignment and Collaboration Issues

Marketing doesn't operate in a vacuum. When internal teams are misaligned or working at cross-purposes, even good marketing struggles to produce results.

Sales/Marketing Silos

Marketing and Sales operating as adversaries instead of allies. I've lost count of how many times I've seen this play out.

Sometimes it's differing metrics—marketing optimizing for clicks while sales cares about closed deals. Sometimes it's structural—marketing reporting to the CRO or VP Sales, which narrows its scope to short-term lead gen and sales support, killing the longer-term strategic work.

That won't show up in a quarter. Or maybe even a year. But the breakdown in effective collaboration will impact revenue.

Assuming Internal Consensus Exists

Leadership teams often assume everyone agrees on positioning, ideal customers, and messaging. They've had the conversations. Everyone nodded. (Here's a tip: nodding isn't alignment.)

But ask Product, Sales, Marketing, and Customer Success separately, and you'll get four different answers. This unstated misalignment shows up in inconsistent external communication—and confuses prospects.

Before you worry about external messaging, get internal alignment sorted. Otherwise, you're just broadcasting confusion at scale.

Ignoring Frontline Insights

The people closest to your customers—Sales, Customer Success, Support—know things your leadership team doesn't. They hear the objections. They know why deals stall. They understand what customers actually value.

Yet many companies fail to systematically gather this insight and share it. They rely on internal assumptions instead of real customer feedback. They miss the opportunity to uncover misalignments between what the business thinks it sells and what customers actually need.

The information is sitting right there. But that would require asking—and actually listening to the answer.

The Better Path

If you've recognized your company in a few of these, you're not alone. These patterns are common precisely because they're easy to fall into.

The fix isn't complicated. But it does require a shift:

• Get clear on who you're for, what makes you different, and how you explain it.

• Build strategy before adding more tactics.

• Empower your marketing leader with access, trust, and a seat at the table.

• Align internally before broadcasting externally.

• Listen to your customers—and the people who talk to them every day.

• Commit to the long game. Invest in awareness and trust with the ones who aren’t buying yet.

Clarity before strategy. Strategy before tactics. It's a sequence, not a suggestion. Skip it at your peril. If you want the full breakdown of why this order matters, start here.

And if you're nodding along—and not just politely—let's talk.