Sales Humor: How to Use it in Your Cold Email Outreach

Use humor with your prospects!
sales humor cover photo
Using humor strategically can have a tremendous impact on your sales success! It can captivate your audience, make a lasting impression, and establish rapport.

However, it's crucial to strike the right balance because if done incorrectly, you might be perceived as someone who lacks situational awareness.

In this blog, we'll guide you through the art of incorporating humor into your cold email outreach in a manner that resonates with your recipients.

Why Using Humor in Sales is a Great Approach to Build Rapport

The first thing we want to do is understand why humor in sales works.

And the answer to that is connection.

Whenever you are reaching out to prospects about your product or service, the main goal is to establish a connection. Find some commonality from which you can build rapport.

You are looking for this when you're researching them as well, but they won't always be as easy as simply having both been alumni of the same university.

So what else do humans need to form a connection with others that is also easy to establish quickly?

You don't have the time or luxury to wine and dine your prospects on a cold email.

But you can send them something that will cause them to crack a smile.

And getting that smile means they start developing a positive relationship with you as a sender.

Because humor does work.

Salesman and stand-up comedian Jon Selig can easily establish the similarities between the two roles in his life.

Salespeople are always trying to get to the pitch or call to action. Just like comedians are always trying to get to the punchline.

In both cases, we employ storytelling to build up value to that pitch or punchline for the audience, so that the pay-off is greater.

And, if you make it a personal mission to get your prospect to smile, they have a good time and feel touched. It's a more personalized approach. Especially if you do enough research to tailor your humor accordingly.

In Yes!: 50 Scientifically Proven Ways to Be Persuasive, authors Noah J. Goldstein, Robert B. Cialdini, and Steven J. Martin revealed some interesting facts:

When performing outreach, if you send a funny, inoffensive cartoon to the person you're negotiating with, those receiving it reported feeling a higher level of trust, which led to a 15% larger profit for companies utilizing humor in this way in their outreach.

A real-life example of using humor in sales is DollarShaveClub. Ahead of their time, and capturing the zeitgeist of subscription services of the early 2010s, they developed just that for razor blades.

At the time, their approach was unconventional and, shall we say, millennial. But it was well worth it. In 2016, Unilvever acquired the company for one billion dollars in cash. And this was because they had seen them build rapport with their target audience via the use of humor.

The infamous "on Wednesdays, we wear pink" from the 2004 comedy Mean Girls can be re-adapted to fit SDRs.

Your SDR manager telling you that on Tuesdays, we prospect at this company, is a fun, unintentional call back to this classic moment.

Tips on Using Humor in Sales

We know, then, that using humor in sales absolutely works to create a connection. We've gone over the similarities, the statistics, and an actual example.

But how do you avoid sticking your foot in your mouth and batting out early?

P.S.: you can write funny the subject lines, and add humor in the cold email copy using these tips!

Here are some do's and don't's to get you started:

Do Use Your Personality

At the end of the day, your prospect is building a relationship, and connecting with you. Not your company or product, but you.

You've found them through research, you've prospected and reached out to them, so simply be yourself.

If there's something funny to you, and you can weave it in accordingly, share it with them!

Having a similar sense of humor is also a good way to qualify your lead for your company overall. You work for them, after all.

Don't Use Dark Jokes

That said, dark or edgy jokes should be used sparingly or not at all.

It is alright to make a mistake if you had a sequence going out with something you did not consider. We can't control how everyone may react.

However, if you know you've made a joke or comment that is quite dark in nature, it is best to avoid it entirely in the B2B world.

This is your prospect's first interaction with you and your company, and you do not want to burn bridges with them before even getting your foot in the door simply because your joke was edgy. It could also give your company a bad reputation, and by word of mouth, it can experience high churn rates.

And remember that, at the end of the day, you are also the face of your company to your prospects.

Do Research For Appropriate References

You already research your prospect for so many more qualities, so why not take the extra bit of time to try to learn about their interests?

Or make a well-educated guess.

A prospect in marketing is likely to appreciate jokes related to SEO, for example. If you find out they went to a particular university or college, you can maybe make a joke about their sports team. Or, if their degree is in something slightly different, you can potentially offer a funny reference based on that!

Taking the time to do this extra bit of research will help you craft the perfect funny approach.

Don't Forget To Research & Don't Assume One Joke Fits All Prospects

Without taking that time, you may quickly find yourself bombing like a comedian with a poor set.

Marketers may enjoy jokes about SEO, but including Operations or Supply Chain leaders in those same sequences would be a mistake.

Segment your audiences, messaging, and jokes accordingly to get the most out of your research and cold emailing.

Do Use Self-deprecating Humor

It's always good to address the elephant in the room. Especially when the elephant is that you're a salesperson trying to book a meeting.

Don't be shy to bring humor to the table based on that.

For a follow-up, starting your email copy with something along the lines of "Hi {{first_name}}, me again, think we keep just missing each other!" can bring enough of a smile to your prospect's face for them to finally respond.

You could also use something from our blog, the history of Hi {first_name}, just kidding.

Don't Be Too Negative

But no one likes a negative Nancy, so don't overdo it with self-deprecating humor, either.

Sarcasm is well and good until it simply makes you appear to be quite an awful person to be around, never mind listening to what you have to say about your product or service.

Too much negativity colors the entire impression of not just you, but your company, so stick to one-off self-deprecating jokes that you run by someone else first!

Do Be Aware of Current World Affairs

When using humor, make sure you're educated about what's going on enough to make that reference.

Whether it's a World Cup, the Olympics, the Oscars, the economy, or something related to Pop Culture, make sure you know what you're talking about. Your prospect might respond based on that.

So keep yourself updated on what's going on, constantly.

Don't Use Sensitive Topics Such as Politics

If you're keeping yourself updated, you should also know that some topics are sensitive and should not be brought up. Least of all when you're trying to sell.

It's best to avoid political jokes or jokes about polarizing topics, especially if they're a reference and not at all related to your field.

If you're unsure, you can always run it by a colleague or manager first!

How to Use Humor in Sales

Use Appropriate GIFs

Perhaps one of the most favored methods by our team, a well-timed, appropriately-used GIF can provide you with a response from a prospect you've tried to engage with multiple times already.

Don't start off with a GIF, but they're a great way to follow up with prospects and provide you with a reaction.

There's a reason LinkedIn added them to DMs – use them well!

To start you off, we do love our it's been 84 years option, especially since so many prospects want to reconnect in the new year – we'll be sending lots of these then!:
sales meme gif

Make Use of Memes to Connect With Your Prospect

A picture truly is worth a thousand words.

Just as in the Yes! book cited above, it is now memes and not inoffensive cartoons that you can send to interest your prospects in getting to know more.

Whether it's a sales meme to share with your fellow SDRs or with your prospects, it's a concise way to share your feelings about the possibility of a meeting while still being humorous.

Now that you're here, check out our tips to keep your SDRs happy and motivated! We also have tips for you, SDRs ;)

And it's a great conversation starter on the web, where most leaders have spent a good chunk of their youth these days.

One you could use is letting your prospect know how you felt after that lovely phone call:
good cold call sales meme

Funny Email Subject Lines Can Get Your Email Opened Faster

Want to stand out in your prospect's inbox?

Well, you need a funny email subject line.

We created a list available to you in this post because subject lines that use humor can truly help you stand out from the crowd from the very beginning.

But they're a tougher nut to crack than they may seem at first glance, so make sure to follow all requirements and suggested approaches to truly make the most of it!


Humor in sales is a vital component that all Sales Development Representatives (SDRs) at SalesPipe embrace and continually experiment with.

We firmly believe that incorporating humor into our sales approach allows us to create a more comfortable and confident environment, enabling us to connect better with potential customers.