Quick: How would you describe your company’s B2B content or email marketing copy?
Professional? Serious? Informative? Maybe even persuasive?
Great — those all have their place.
But what about … funny?
If you’re a B2B marketer juggling sales meetings, marketing reports, and writing content in between Slack pings, humor might feel like a luxury you don’t have time for. Or worse, a risky move that could make you look unprofessional.
But the truth is, your audience is not some pretend persona with an alliterative name who only lives in a slide deck. Your audience is, well, people. And not only do people like to laugh, but it turns out laughter is a terrific way to form strong bonds and a sense of community. And isn’t that what all of us marketers are trying to do?
Let’s be honest: A lot of B2B content marketing sounds like it was written by a committee after reading a thesaurus over a sad desk lunch. Somewhere along the way, we all got the memo that being credible meant being serious. So we cranked up the buzzwords and dialed down the personality.
The result? Snooze-fest content. The kind that makes even caffeine give up.
But in a world where your audience scrolls past dozens of dull ads, sales emails, and landing pages each day, humor stands out. It’s a pattern-breaker. It gets attention. It says, “Hey, we’re not like every other brand begging for your click.”
And it makes people happy.
Laughter triggers dopamine — the “feel-good” chemical tied to memory and engagement. That means your message doesn’t just entertain; it sticks. People remember the brand that made them smile, not the one that sounded like it was written by a tax form.
After all, who would you rather work with: the brand that sounds like an instruction manual, or the one that makes you feel like a human being?
I’ll be honest: I wasn’t always waving the funny flag in my writing.
Back when I was a small-town newspaper reporter, humor wasn’t exactly encouraged. Let’s just say it’s hard to crack a joke in a piece about city council zoning disputes. (Believe me, I tried.)
But everything changed when I started writing “on hold” messaging — you know, the audio people hear when they’re stuck waiting on the phone. If that sounds like a tough crowd, you’re absolutely right. These are people who would literally rather do anything else, including argue with a chatbot or listen to elevator music on repeat.
My job? Make them laugh.
So instead of lifeless updates, I wrote quick, clever lines with unexpected humor and a little personality. The goal wasn’t to become the next stand-up comic. It was to make the wait feel like less of a punishment and more like a pleasant surprise. And it worked. I once had a caller ask to be put back on hold just to finish listening to the message. (Yes, really.)
That’s when I realized humor isn’t just decoration. It’s connection.
It doesn’t have to be over-the-top, either. Sometimes it’s as simple as seeing a boring B2B offer from a funny angle. Like this promo I once wrote for a pack of flashlights:
That tone isn’t for everyone. But the strategy is universal:
Even a single sentence of humor — a witty subject line, a clever CTA — can help your B2B marketing content stand out.
More recently, I worked with our client ClearSale on an email newsletter that goes out to their B2B partners. The newsletter is sent by Faye McEachern, their Director of Partnerships — a woman with a great sense of humor and a laugh that can light up a Zoom room.
Because Faye’s job is all about building relationships with her partners, we really wanted Faye’s personality to shine through. And so we included well-placed jokes, quirky metaphors, and the occasional meme. Not only did engagement improve, but open rates jumped. After reading each newsletter draft, Faye would regularly message me, saying things like, “You made me howl this month.”
The best part? We didn’t overhaul the company’s brand voice. We just dialed up the humanity.
Let’s look at a few brands that got it right — and a couple that missed the mark.
Mailchimp: “Did You Mean Mailchimp?”
Mailchimp leaned into the fact that people kept mispronouncing their name. The result? A surreal, delightful campaign featuring faux brands like MailShrimp and KaleLimp.
👉 Watch it here:
Dissolve: “This Is a Generic Brand Video”
Dissolve turned the “stock video montage” trope into a parody masterpiece. It was funny, painfully accurate, and wildly effective.
👉 Watch it here:
Zendesk: “Sh*t Support Agents Say”
Zendesk embraced the daily chaos of customer support with a hilarious, profanity-censored video that showed they get it.
👉 Watch it here:
Slack: Quirky Workplace Pain Points
Slack nails everyday frustrations with status toggling, passive-aggressive Slackbot reminders, and endless notifications. Their humor is subtle but highly relatable.
Microsoft: “The Browser You Loved to Hate”
A self-deprecating campaign trying to win back Internet Explorer users. Clever in theory, but many felt it glossed over long-standing frustrations.
👉 Watch it here:
TeamWork Online: MH370 Tweet
In 2014, TeamWork Online compared a missing job candidate to the missing Malaysian Airlines flight. The backlash was swift and deserved.
👉 Archived Tweet here:
Even "serious" industries can be funny – but your humor needs to feel like you.
Funny doesn’t mean sloppy. Your audience still needs to believe you’re competent.
You need to know what your audience finds funny — and what will fall flat.
Get a second opinion. Or three.
If you want your content to be remembered, shared, and — dare I say — enjoyed, then yes, it’s time to give humor a seat at the table.
You don’t need to be the funniest brand on the internet. You just need to be the one that sounds like a real human. One your audience actually wants to hear from again.
So start small:
Test what works. Tweak what doesn’t. And if something totally bombs? Congrats — you’ve just joined the club of brands brave enough to try.
When done right, humor doesn’t just make your B2B copywriting better. It makes your brand stickier. And in a sea of safe, same-sounding content, a little levity might be your best competitive advantage.
Ready to write content that makes people smile and say yes?
👉 Grab our Persuasive Copywriting Guide for more tips, tricks, and proven frameworks.
No knock-knock jokes required. Unless you're into that.