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Add the Tee-Hee to B2B: How Humor and Wit Drive Email Engagement

Hear that? That's the sound of hundreds of incoming emails trying to grab a tiny slice of your attention in an inbox that’s mostly unread. If you feel like your inbox is drowning, it's because it probably is.

Ask yourself “When was the last time an email actually caught your attention?”

Email marketers need to try harder than ever to cut through the clutter so we stress about subject lines and email templates to push engagement up a mere decimal point. We can all agree that an open isn't trivial, so what do we focus on?

  • Are you engaging with personalized content?

  • Is there interest in your product or service?

  • Are you creating conversations that influence pipeline?

Think beyond vanity metrics like open and click-through rates if you really want to engage and delight.

At Uberflip, I have the challenge (and pleasure) of marketing to marketers. The very people (like you and I) who do this for a living. We're harder to impress. We know all the best practices and tactics so you'll have to be extra good to get our attention.

B2B ≠ Boring

B2B marketing is notorious for being overly serious, corporate, and a lot of times boring. That's a reputation we can change as B2B marketers.

As a demand generation marketer, it's easy to focus on lead engagement and driving more MQLs into your pipeline that you forget that you're marketing to humans who love to laugh, be entertained and gain knowledge. That's what our content and emails should do for our prospects. Let's learn how to engage uniquely, not just click and convert.

How I Use Humor to Drive Email Engagement

A little bit of cleverness goes a long way. That's why I pick my brain every time I need to send an email. How can my emails stand out? I mix a little humor and wit into my email engagement strategy when the opportunity arises.

Marketing to B2B marketers can be tough but my biggest email wins have come from the boldest departures from regular, safe design. You have to be fearless, and I'm thankful for the adventurous leadership on my team who support creativity.

But I cannot stress enough that humor should not overrule your goal. Don't be clickbait. Don't clutter up your copy with so much cuteness that people can't see the point anymore. Opens are great but if your subscriber opens something they did not expect, there's an unsubscribe coming your way—or better yet, an angry all-caps reply. (You know what I'm talking about!)



But don't let fear limit your creativity.

Huge lesson: Some will hate, but most will love you. I get negative feedback all the time. But that is so insignificant compared to the dozens of marketers who email me with high-fives and amazing compliments.

I had to ask myself, "Would I rather hear crickets after every safe, average email I send?" or get an inbox flooded with responses that trigger conversations about marketing and Uberflip? I set myself on an incredible journey and you want to learn something ridiculous? Everyone loves to laugh.

Three Simple Rules of Email Engagement 

  1. Treat your prospects like people, not MQLs.

  2. Emails are an extension of your brand experience. Invest in personality.

  3. Earn trust, not conversions and welcome conversations.

And want to learn something even more ridiculous? You can be clear and not boring.

What better way to warm up your prospects than by making them smile? Humor is inviting. It breaks down barriers. It sparks chemistry between the marketer and reader and lets them know that we're fun people to work with.

I've compiled a few examples of where puns and personality have created opportunities, delighted subscribers and engaged our audience in conversations. My goal was to translate Uberflip's internal culture into our emails. Let’s take a look:

Example 1: Humor sparks conversations

This simple, yet fun email generated nearly 4x the usual replies.



One of the responders let us know that she wasn't the right contact for the topic of this content.

Noted—swap her persona!

Be consistent!

Continuous Engagement:

A little bit of negativity never hurt anybody:

Like they say, some will hate you but most will love you.

Another email:

and the replies began pouring in, in just a few minutes!

Again, consistency is key!

Prioritize your brand experience. People remember how you made them feel.

Example 2: A tad bit of personality can influence pipeline

This one was a myriad of personification, seasonal pursuit topped with some witty cuteness—but still very relevant to the subscriber. They are all users of Terminus.

The body and copy of the email drove opportunities:

This time, we plugged it in the subject line:

Besides being funny, your email subject line needs to be relevant and personalized to your prospects' recent experiences. If we sent a random email with Seth Godin's name, it wouldn't have performed as well as this one that was sent to prospects who had just attended an event where he spoke.

Example 3: Post-event follow-ups are brutal inbox invasions for attendees. Stand out by making it fun.

And when your team creates a bold experience in-person, your follow-up should be an extension of this experience.

If they weren't talking to you at your booth, they'll definitely be talking now. Sometimes you just have to commit to your marketing.

Example 4: Turn something serious and boring by nature into something light-hearted and relatable.

GDPR had taken the marketing world by storm. Everyone was talking about it and sending their consent emails and privacy policy updates. We decided there needed to be some light, relatable humor attached to it. How can we get them to re-engage with us? Remind them why they joined us in the first place!


This email stirred up dozens of replies—from those wanting to re-engage and from those who reached out to compliment the creativity.

Even people who were unsubscribing wanted to let us know:

Example 5: Then there are people you don't expect to engage

A response from your CMO :)

And how about some Ann Handley?

Example 6: Building really witty and humorous emails builds you recognition and funny enough, authority.

The emails that get featured in publications and marketing blogs aren't our regular emails. They're the emails that get the "ha-ha's" and smirks, and sometimes even the borderline risqué ones get some attention. Here are a few that recently got noticed:

The bottom line? Using humor, being creative, and showing your human side can all be smart marketing techniques that you are not leveraging currently. Start small and see where the journey takes you. Make the communication of ideas frictionless—the system that works for you is the system that works.

Let's end this off with a cheesy marketing joke:

Why do subscribers hate religious emails?


Because they're always trying to convert them.

Don't be those guys.


Arabi Siva

About the Author

As Marketing Programs Manager, Arabi runs the revenue marketing and demand gen programs at Uberflip, where conversion optimization, emails, webinars, and marketing automation are the bane of her existence. They say curiosity killed the cat, but Arabi’s curiosity killed her inbox as she’s guilty of subscribing to dozens of modern marketing, startup tech, social impact, and design thinking content. And not to mention, she’s crazy about puns and adds the sass to SaaS.

Profile Photo of Arabi Sivananthalingam