11 Funny but Effective Sales Emails by the HubSpot Sales Team [Templates]

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Aja Frost
Aja Frost



Are you sending boring, generic emails that look just like the past 100 your prospects have gotten from reps? Or are you trying to stand out from the crowd?


We've rounded up a handful of battle-tested, clever sales emails from HubSpot sales reps -- and included a few new templates for you to try out for yourself.

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How Humor Can Make Sales Emails More Effective

When it comes to sales emails, a little levity goes a long way. Most messages are straightforward and serious -- and boring. Adding a fun twist to their outreach helps reps distinguish themselves from the competition and make their pitch more memorable.

In addition, humor usually puts recipients in a better mood. Once their prospects are smiling, salespeople usually have a far better shot of getting time on their calendars.

That being said, no gimmick can make up for a bad sales process. If reps aren't capable of asking probing questions, diagnosing their prospect's needs, consistently adding value throughout the conversation, tailoring their pitch to the individual buyer's situation, and surfacing urgency, an attention-grabbing email will make zero difference to their bottom line.

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1. The funny sales pitch

According to Yes! 50 Scientifically Proven Ways to Be More Persuasive, businesspeople who sent a funny, inoffensive cartoon to their negotiation partners before negotiating generated higher levels of trust and 15% larger profits than those who didn’t send a cartoon.

Salespeople can leverage the same trust-building effects by including a cartoon in their outreach email.

[Prospect name], are you struggling with [challenge]?

Hi [prospect name],

Some salespeople are all about how you can help them ...

Sales cartoon for funny emails

But I’m interested in your objectives. In working with similar companies [in X industry or vertical/of similar size in X region], I’ve found many struggle with [major business challenge].

If this is something you’re challenged with as well, have you considered [strategy/tip]? I have some other ideas that might help too.


[Your name]

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2. The response to “we’re all set” or “no thanks”:

Hearing this standard objection doesn’t necessarily mean there’s no opportunity. Use this template to make buyers think twice about brushing you off. If they’re truly not in a position to buy, they’ll remember you when the timing is better. And if they are a good fit, disarming them with a funny meme will likely lead them to think, “Hmm, this doesn’t seem like the average salesperson. Maybe I should give them a chance after all.”

One last question

Hi [prospect name],

hilarious sales email gif


[Your name]

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Matt Hambor, Inbound Marketing Specialist

3. The witty email

To immediately differentiate yourself from other salespeople -- and hopefully, make the buyer laugh -- send them a tongue-in-cheek sales email as a follow-up to the compelling event.

[Prospect name], I hate sales emails

Yes, I’m sending you one right now, but in my defense it’s because you [requested more information on X/Y trigger event just occurred].

If you’re not interested in [accomplishing X results/discussing relevant challenge or opportunity], please let me know so I can stop being a hypocrite.

Seriously, every time I click “Send,” it pains me. Help stop my suffering and find a time on my calendar here.


[Your name]

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Sam Belt, Senior Sales Partner Manager

4. The clever email

Walking around the conference floor isn't usually the most scintillating activity in the world. Use this template to provoke your prospect's curiosity and make a conversation with you seem more fun than the typical booth chat. Even if they don't respond, they're likelier to stop by when they see your company's name. 

Cheer [salesperson] up at [conference]?

Hey [prospect name],

Saw you were involved with [organization]. I'm curious if you're going to the [conference]? We'd love to meet up with your team. I know one guy on my team would especially love to meet up:

funny gif to send a prospect

Want to book a quick side meeting or swap some text and meet up at our booth?

[Your name] a.k.a. [nickname] (this will make sense when you come to the booth)

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Drew Healey, Sales Development Team Lead, LeadIQ

5. The no-B.S. email

Rather than pretending your previous (unsuccessful) contact attempts never happened, bring them out into the open. Then, hook the prospect by discussing why this time is different.


Hi [prospect name],

I’ve reached out to [company] several times over the past few years. What I talked about clearly didn’t resonate. I heard the collective yawn and have made some changes.

This partnership is now about three simple things:

  1. Helping you improve [X area of business]
  2. Helping you solve [X challenge]
  3. Helping you achieve [X results]

If the above sounds interesting, let's connect so I can provide more information on how we have started a new chapter.


[Your name]

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Claire Chazen, Channel Account Manager, HubSpot Agency Partner Program

6. The light-hearted email

Traditional guilt-tripping doesn’t work. Your prospect will be far likelier to reschedule if you make a light-hearted reference to the no-show.

Just like Ross Geller's Prom Night ...

Hi [prospect name],

We haven't been able to reschedule our [product] meeting and it's reminding me a lot of when Rachel stood up Ross on Prom night ...

funny gif for salesperson email

Jokes aside, I was curious if you are still interested in putting time back on the calendar for us to discuss strategies for [achieving X goal or outcome].

Here's my calendar if you'd like to discuss in more detail. If you're simply not interested anymore, not a problem, just let me know so I can return my tuxedo. :)


[Your name]

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James Hylas, Senior Account Executive, HubSpot Sales Solutions

7. The hilarious email to a prospect who ghosted

Few things are more frustrating than a promising prospect who abruptly stops returning your calls and emails. Sometimes, an Adele reference is what you need to bring them back.

Hello from the other side

Hello [prospect name],

I must have called a thousand times ...

salesperson ghosted email

On a more serious note, last time we talked about [pain] and how [product] could help [drive X results/accomplish X goal] over [specific timeframe].

Are you still interested in continuing our discussion? If not, please let me know so I can stop blasting Adele.


[Your name]

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Gary Valenti, Account Executive, HubSpot Sales Solutions

8. The Fun Friday email

No matter where you work, the office feels different on Friday. Everyone's a little more relaxed and a little less uptight. Take advantage of the laidback mood, and shoot your prospect a Friday-themed message that won't hurt their ears.

9. The cheerful email

Does your prospect seem like they'd be responsive to a little cheer? Send them this upbeat email.

10. The "no rush" email

Want to make sure your prospect knows they've got plenty of time (within reason) to learn about whether your company and product is right for them? Try this template, that uses pop culture to set the right tone. 

11. The fill-in-the-blanks email

Just need to get them to open the email in order to pique their interest? Try this template to open a conversation with a prospect.

Not every buyer will be responsive to a humorous or offbeat email. Before sending one of these templates to your prospect, consider what you know about their personality and preferences from previous interactions or their social media accounts. If they seem more conservative or buttoned-up than your average buyer, a more traditional sales email might be wise.

But as CEO of Sales Hacker Max Altuscher says, "Don't be overly cautious. For the most part, if a prospect is just not answering you no matter what you do, sending a funny message is a great last-ditch effort."

Want more follow-up sales email templates to send instead of "checking in?" This should help.

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