How to Turn Punchlines into Profit: 3 Strategies for Humor-Infused Sales

The only thing colder than most outreach…

…is the shoulder prospects give it. 

I’m Jon Selig—half sales guy, half stand-up comedian, and all parental disappointment. My 12 years in sales was a well-paid internship for my career in stand-up comedy.

I merged my two backgrounds to create “Comedy Writing for Revenue Teams”. I deliver both memorable messaging and sales enablement through the process of crafting jokes. Ironically - this isn’t one.

These are my three tips for how to inject humor into your sales process.

What Stand-Up Comedy Taught Me About the Cold Call

I started my sales career when a cold caller’s tech stack was a CRM and a landline. I would rattle off a big, fancy script just for prospects to cut me off halfway through my spiel. 

I realized I needed to get to the point FAST - like, within 5-10 seconds. And do it in a way that grabs their attention.

When I started performing stand-up comedy, I was confronted with the same truths.

I had a “generous” 15-20 seconds to capture an audience’s attention by making them laugh and getting them on my side. I’d achieve this with material that they relate to—their struggles, their experiences, and the things, people and places they felt strongly about.

I needed to make it less about myself…and a lot more about them.

Our cold outreach (calls, emails, etc.) needs to show our prospects that we understand: 

1. How a pain or problem they’re experiencing is impacting them
2. What success looks like for them
3. How eliminating the pain will help them achieve success

Short, thoughtful, relevant humor can allow SDRs to achieve all three.

Here are three of the most effective ways salespeople can transform a boring business problem into something simple that brings a smile to our prospects and, hopefully, a closed-won deal through your pipeline.

#1: Roast your prospect's pains

The comedy roast consists of comedians subjecting a guest of honor to jokes that highlight their worst behaviors, qualities & attributes - in a loving, playful way.

Swap out a famous guest of honor for a prospect’s pain point—and you’ll have their attention. The humor is designed to show your target persona that you understand their challenges. 

Doing it in a clever way, designed to elicit a smile, paints a memorable picture — and not necessarily because it’s “laugh-out-loud” funny - but because it’s unique from all other messaging your prospect receives.

Consider the following joke I crafted for a SaaS that helps CMOs manage their privacy compliance efforts, highlighting how their CEOs may not appreciate the need to invest in tools: 

“CEO’s are like my parents.

The only thing they understand less than technology — is privacy.”

Not a joke that will end up in anyone’s hour-long special, but it:

• Provokes curiosity 
• Highlights something SPECIFIC which a prospect relates to
• Tells a story
• Surprises the reader (or listener)
• Elicits an emotional reaction (hopefully a chuckle)

#2: Make creative comparisons

Some of the simplest humor compares two very different things to each other (physical objects, people, places, concepts, etc.) in a short, snappy one-liner.

Here are examples of a few icebreakers I wrote for clients to highlight very specific circumstances & challenges their prospects face:

"Privacy has generated more positive feelings for Apollo than Ted Lasso."

Even though they’re two very different things, both the show “Ted Lasso” and Apple making security both a feature and a benefit have made customers feel good about their brand.

"The only thing more complicated than network architecture...is the excuse you'll create to absolve yourself when it fails."

In this case, I compare a problem I can solve for my target persona to an exaggerated consequence of not solving the problem.

And by linking them together it paints a picture or tells a story.

To achieve this, open a blank doc (or grab a piece of paper!).  

Write and unpack as much as you can say about the problem.  List all the impacts, outcomes, consequences, and risks of not solving the problem that will ultimately cost them time and/or money.

Get as granular and specific as possible.  

In order to paint that right picture, you’ll need to get creative with words and phrases to link how the problem you solve leads to an undesirable outcome that prevents your target persona from reaching their objective.

There are no hacks to creativity. Brainstorm all your knowledge. Get it all on paper.  Review the words and phrases.  Find new ways to use them or other things that describe them. Think outside the box. Talk things out. And capture THOSE ideas on paper.

But if you’re looking for the simplest, most useful kind of one-liner…

#3: "Cold openers": Bespoke icebreakers for cold outreach

Prospects respect transparency - like being up-front with your prospects that your outreach is unsolicited—aka “cold”. 

Other than “unsolicited” and low temperature, the word “cold” is used in many idioms and metaphors that describe emotional reactions.

For example: when we’re afraid of something, we break into a "cold sweat". 

Think of the specific problem you can eliminate for your prospects. Ask yourself: 

Why, how, or when does this problem frighten your prospects? (i.e. how does it prevent clients from doing business with them? How does it cause harm to their (or a stakeholder’s) objectives?)

Paint a very specific, clear picture to show you understand why they (or a key stakeholder) could be afraid of the problem.  

For example, if I was cold calling or emailing CROs about how I help with call reluctance, I’d say:

"This call/email is colder than an SDR's feet on their first day dialing."

It’s short, quick, relevant, offers transparency, and a common challenge that they are likely struggling with.

If we were to see this in action for a cold call, I’d suggest stating your name, and who you’re calling from before zinging your prospect answering the call.

“Hi (first name}...this is Jon with Apollo, and this call’s colder than _____.”

Another strategy I encourage folks to employ is to include the setup in the email subject line.

Subject: "This email's colder than..."

Would you be tempted to open the email to see what follows the three-dot ellipsis?

Odds are it will stand out, catch your prospects’ eyes, provoke curiosity, and prompt them to read on.

Humor in sales isn’t a risk—it brings the X factor

Embracing humor in sales has always been a game-changer for many successful sellers, but many still hesitate to incorporate it into their go-to-market strategies, fearing the risks involved.

While injecting silly remarks can be a gamble, injecting carefully-crafted humor, based on genuine truths and professional experiences, is a golden ticket to standing out and creating genuine human relationships.