Why Your Marketing Team Needs A Rule-Breaker

Want to continue being Joe Average? Keep following the “best practices.” That’ll keep you average, no problem. Every brand should have a marketing maverick to make bolder ideas without creating chaos.

Shock horror. B2B marketing has a reputation problem. In the UK, 82% of business leaders find B2B marketing boring and repetitive, while 88% would like to see a bolder, more contrarian, or more provocative approach.

So, what’s behind this problem? For the most part, it’s that B2B brands tend to be risk-averse, sticking firmly to so-called “best practices.” The thing is, those best practices are only really best for the biggest brands with the biggest budgets. They’re fat, lazy and gorging on profits. They’re happy to play it safe, because, for them, the status quo just works.

And sameness really is a big problem in B2B. Almost every brand has the same funnels, the same AI-assisted content, and the same approach to “thought leadership.” The outcome is an endless sea of lookalike, product-led content where marketing gets more and more automated – oh, and soulless to boot.

But there’s good news. B2B buyers are yearning for a braver marketing approach. Yay!

Injecting emotion and humanity is an opportunity for those willing to break the mold. That’s doubly important for Underdog brands that aren’t going to get heard if they’re just “playing it safe.”

The fastest route to “meh”… Best practice.

How many times have you seen lead magnets promising the same AI-powered, end-to-end, full-stack solutions and seamless, integrated offerings? These tired examples of corporate speak might feel safe and proven to big brand marketing teams, but they’re also what make potential buyers tune out. For an Underdog brand – nowhere near the top of its category – such statements sound even more cringe.

The Underdog wins by doing what the biggest brands either can’t, won’t, or daren’t – but most teams aren’t structurally set up for that. They’re stuck following the same playbooks as the big guys, focusing more on awareness than anything else. Those “best practices” see teams churning out “thought leadership” content that doesn’t challenge assumptions and reads like a sales pitch.

But true thought leadership has changed. It’s no longer a one-way broadcast, but a conversation with potential customers. Effective marketing focuses on the customer’s problem and outcome by aligning with their pain points. But if you’re the Underdog, that’s still not enough. You need to be authentic and relatable, not just as another B2B vendor, but on a human level too.

When everyone’s the same, a maverick stands out

Enter the marketing maverick – the one who questions how things are done, proposes alternatives to doomed “best practices,” and pushes for decisive action. They’re the heretics, tapping into uncommon customer truths and challenging assumptions. They’re willing to take creative risks, even if that means being provocative. In short, they’re a pain in the arse.

The maverick will alienate people. And that’s fine. After all, they’re not trying to please everyone. They leave that to the category leader – the big brand names customers default to because they don’t know any better – at least, not yet.

Take Mailchimp, the US martech company and a quintessential B2B brand, for example. Realizing that people often mispronounced their brand name, they leaned into the mistake and launched a playful campaign of fake brands that rhymed with Mailchimp. They even published a song called MailShrimp. It was bold, it was absurd, and it was hugely effective. No one else in the email software space, which isn’t exactly known for its memorable advertising, had ever done anything like it. It proved that humor, despite being a rare commodity in the B2B world, can work. Because, after all, humor is human.

But pick your battles (and watch your tone)

Of course, not every maverick needs to be funny. If you're selling insurance or medical devices to hospitals, humor might be a terrible idea. But you can still strike an emotional chord.

In more serious categories, the best maverick move is often being boring in the best possible way: Where a category leader hides behind jargon, the Underdog might offer the clearest pricing, the simplest contracts, and the least legal friction. It might make leadership squirm – but it’s exactly the kind of clarity customers look for (and remember).

Radical transparency is another classic maverick move. In September 2025, cybersecurity company Cloudflare published a detailed blog post on the impact of a breach, where an outsider gained access to their Salesforce instance. Instead of brushing it under the carpet – as some brands might – they explained what happened, how they dealt with it, and what customers needed to know.

For the Underdog, being a maverick might mean being explicit about what you don’t do. Again, it’ll make the head of legal squirm… and that’s always fun. Just remember: they’re not the customer. Clarity builds trust a lot quicker than the vague “enterprise-grade” claims that category leaders tend to like – and it helps trim the fat, too. When you say, “we don’t do X,” you get the right buyers leaning in.

Give them room to run, without burning the place down

Being rebellious isn’t about being an edgelord. You want to make waves, not sink ships.

That usually requires a structural fix. Start by cutting out the stakeholder circus. That’s right, even the “reaaaally important” ones. If a dozen people all get a vote, feedback arrives late, and the loudest opinion – not always the best one, by the way – is the one that gets listened to. Fewer cooks often means better broths (and faster dinners).

Don't run marketing by “vibes approval” either. It's the fastest way to kill good work with useless feedback. If stakeholders are offering lines like “I'm not sure customers will like this” without evidence, or “it doesn't feel very us” without defining “us,” then you don’t have the right people in your proverbial kitchen. The only opinions that matter are the ones grounded in customer truth – those are the people closest to the market, not the ones furthest from it. Otherwise, all you're creating is a system where the safest idea wins, and work that’s safe, bland, and instantly forgettable.

None of this means there are no boundaries. You still need red lines – just don’t let legal become creative director. Their job is to define what can be claimed, what needs disclaimers, and what requires substantiation. Marketing should be free to market boldly within those guardrails (as opposed to handcuffs).

The maverick manifesto: Pick the right person, build the right structure

Ultimately, being a maverick is about experimentation. If you hire a maverick only to treat them like a badly behaved intern, all you’ll end up with is a scapegoat-in-waiting. But pick the wrong person, and you'll spend your time fighting fires instead of making progress.

So, what makes the right person? Well, the best mavericks are obsessed with the customer. They’re comfortable with ambiguity, and confident – perhaps even cocky – enough to push back on internal politics. They question standard process because they see a better way, rather than just for the sake of it. Most importantly, they've got to have the judgment to know when a risk is smart versus reckless. You want a provocateur, not a pyromaniac.

Once you've found this person (they're not unicorns, I promise), it’s important to give them the structure they need to succeed – and then get out of the way. Here's what that looks like:

1. Shrink the decision room (again): The Underdog’s biggest advantage is speed. You only need four people to change your business – the CEO, head of marketing, someone on the front line, and someone who actually speaks to customers. Everyone else can leave the room.
2. Use a one-page “maverick memo”: Your maverick doesn’t need a 30-slide deck to explain their ideas. They need a plan that defines the goals, the current reality, what to test, and the smallest change they can ship in seven days. Legal's red lines should already be clear.
3. Run campaigns on a drumbeat: The Underdog won’t win by putting all their eggs in one basket. It’s important to maintain momentum, so run a few small campaigns over a week or two – pick the winners, then double down on what works.
4. Keep the customer center stage: Stop outsourcing your customers to a persona doc. Including someone who actually has facetime with your customers is a non-negotiable. That person is your anti-BS alarm, calling out big ideas that are really just internal vanity metrics.
5. Don’t forget the safety valve: You need two lanes: a sandbox for fast experiments, and a production lane for scaling what works. If everything has to go through production-level control, your maverick will die of old age before the campaign ever sees daylight.
6. Track two scoreboards: Keep tracking the business metrics the C-suite cares about – win-rate, qualified leads, sales cycle speed. But pair them with learning metrics for the maverick: did it ship, did the message land, what surprised you? Keep those well away from the ROI police.
7. Reward intelligent failures: A maverick should be allowed to get things wrong. That's their job description. If “does everyone like it” is the barometer for success, you've lost the plot. Reward the failures that teach you something, as they’re vital insight into what actually works.

Marketing mavericks have become essential for the teams stuck in conventional thinking – even more so for the Underdog. As a brand with less budget, a smaller footprint, and zero incumbent advantage, you simply can't afford to play it safe and expect to claim mental availability. Because if you’re the Underdog, “safe” is just another word for invisible.