A deeper dive

Comp plans aside, there’s a huge overlap between sales and stand-up comedy.

“Comedy Writing for Revenue Teams” shares the skills, processes, and methods stand-up comedians use to connect with their audiences…

…so your team can better connect with yours.  

Our goal isn’t to “get funny”.

I use the humor-crafting process as a mechanism to help sellers and marketers better understand your prospects and articulate why they should give you their attention and time.

That said, should anyone get funnier – hold me responsible.

 Go deeper:

Why is the process valuable?

The process of crafting short-form humor (aka “jokes” aka “icebreakers”) that highlights problems you eliminate for your prospects reverse-engineers a deeper understanding of:

– Your target persona/avatar

– How they’re impacted by those problems 

– Memorable messaging that shows empathy around each of the above.

Stand-up comedians who generate laugh after laugh do a good job of empathizing with their audience’s struggles & anxieties. 

Eliciting laughter – an emotional reaction to a comedian’s observations or point-of-view – earns attention & builds trust.

Whether or not they can make prospects laugh, go-to-market professionals need to master the same skill.

Sellers and marketers need to highlight problems they solve to elicit emotional reactions from prospects.

Short-form humor (or one-liners or icebreakers or jokes) are:

…short, quick messages that…

…highlight painful truths your prospect struggles with…

…which you can eliminate for them.

Why are the outputs valuable?

Whether it’s over a cold call, at a trade show/conference, over an email, or a countless other channels…

…we have mere seconds to 1) hook our prospects’ attention, 2)  say something of relevance and 3) elicit an emotional reaction from them…that provokes a response.

If crafted well, humor can:

– Build credibility

– Help you to stand out in a noisy market

Check a few jokes to see what I mean.

Being memorable and credible wherever you engage prospects is critical.

To conceive and craft that messaging, your team needs to have a firm grasp on why you matter to prospects.

Without either, they won’t have a chance to uncover or close opportunities.

What ingredients are needed to elicit emotional reactions from your buyers?

Knowing your audience

Understanding your ideal customer and what makes them tick.


The right joke shows your buyer that you understand their world & challenges.


B2B needs creativity. We'll get those frozen juices flowing, even after this workshop.



Why a problem sucks

We'll dig deep into the problems you solve for your buyers and their business & emotional impacts.​

Delivery & timing

In comedy and sales, timing's everything. Practice finds the rhythm.


Good jokes paint pictures, tell stories, and get buyers saying "that's funny because it's true".

Simple language and phrasing

Buzzwords suck. Break free from the evil Buzz-Wordington and speak in simpler English.

18 Learnings, Takeaways, Skills

Stand-ups earn attention & trust from audiences by creatively shining a light on their day-to-day pains, truths, and absurdities, with laughter being an emotion reaction to them.

The process of crafting humor specifically around the problems you eliminate for prospects, reverse-engineers a deeper understanding of your target persona/avatar, how they're impacted by those problems, and leaves behind memorable messaging that shows prospects that you really get them.


A Deeper understanding of your target buyers' Objectives

Comedians can’t make audiences laugh if they don’t know what makes them tick. They need to figure out what commonalities unite them.

Your target personas comprise an audience and sellers/marketers can’t be relevant unless they understand shared commonalities.

Together, we’ll map out everything about you your targeted personas: 

What matters to them, their objectives, and broad challenges, how all of the above impact their emotions – so we can better know which of their buttons to push.


A Deeper understanding of your target buyers' Emotions

Laughter’s an emotional reaction to to frustration, anxiety, and fear caused by pain. 

To craft some humor, we’ll need to work through how problems you solve impact which emotions, and why.




Deeper insights into problems you solve

Can your team help your buyers understand why problems you solve are impacting them beyond costing them time & money or preventing them from making more money?

Salespeople in particular need to master the impacts, risks, and consequences of not solving problems, and be able articulate them in a granular – yet clear- fashion of how they impact your buyer’s objectives, their key stakeholders, and everyone’s emotions.

Together, team members will share and disseminate their collective insight



Context on "Noise"

It’s loud out there!

Your team will gain a new appreciation understanding of the obstacles associated with capturing your prospects’ attention.


An escape from buzzwords

This process will help your team  escape the clutches of the evil “Buzz Wordington”, enabling them to be more human, fluid, and effective communicators.


A framework for creative messaging

If you can’t be funny – at least be different. Your team will get a step-by-step process on how to take an impactful point, smash it into bits, and mold it into something credible and memorable.


Jokewriting 101

Humor is formulaic. 

We’ll break down the different types of jokes, how they work, share examples of how they can be applied to connect with your prospects, and how to build your own.


The psychology of funny

Different people laugh at different things for different reasons. We’ll break down why & what people laugh at, and why & how the right joke can grab attention, shows subject matter expertise, and builds likability and trust.


How to be tasteful

We’ll talk about “The line”. and reps will gain an understanding of professional limits, and what can and CANNOT be said to prospects.


A playbook of memorable messaging

A tasteful opener can be adapted for your particular go-to-market needs.

Your team (and possibly I) will craft a funnel of humor.

When it’s over, your team will receive a playbook for cold call scripts, cold email, social selling, demos, discovery calls and any other circumstance you see fit – based on 6 selected jokes.


email sequences

Crafting new, engaging email sequences that hook attention’s always a challenge.

Within the playbook will be a sequence of six emails – each built from selected jokes which came out of our efforts.


Content for social

Want memes for company socials?

Need content – including scripts for videos – for your team’s social selling efforts?

Humor hooks & delights and what follows educates and delights.


Peer learning & Team building

Participants share tribal knowledge and plug each other’s gaps and collaborate with colleagues from different teams to accomplish their objectives.


A creative experience

People love being creative, but often don’t have the opportunity. Your team will thank you for giving them a chance to stretch their creative muscles and being shown a process to unlocks it.


A confidence boost

To this point, sellers have gained new insight into your buyers, the business challenges you address, and have crafted messaging in language they feel comfortable with. They’ll get further away from their comfort zones to their peers in an “Open Mic” where failure’s part of the process. All of the above is designed to prep them for having easier and better conversations.



Growth – and self-confidence can’t happen without some discomfort… 

…and nothing’s more uncomfortable than trying to make your peers laugh with a scripted bit of humor. 

 They’ll get further away from their comfort zones via an “Open Mic” where failure’s part of the process.


 All of the above is designed to prep them for having easier and better conversations.



It’s not what you say, it’s how you say it. 

Once a joke’s funny on-paper, it’s up to participants to “sell” the joke to their peers. 

Reps will get some time to practice in their breakout group before delivering to their peers.


A unique facilitator

You’ll get comedic input and advisory services from a guy who’s too dysfunctional for your sales team and too functional for the world of comedy.

Use Cases

“Why do this?” you ask.

Five good reasons. Take your pick or more than one.

How this helps your team's:

Onboarding new reps and everboarding tenured ones

Consider: Most sales pros sell stuff they’ve never used, to people whose jobs they’ve never had, in industries they’ve never worked, making it hard to relate and earn trust.

Fun fact: The goal of a training and workshop isn’t to transform your reps into a pack of Seinfelds.

If they assemble a quality, impactful bit of humor that will help them stand-out with prospects – fantastic.

But the real value’s in the process they’ll undertake to assemble it. 

The mission of crafting creative messaging that shines a light on pains your organization eliminates for prospects, forces team members to master everything around:

  • Your audience (i.e. your “target persona” or “avatar”)
  • The pains you eliminate for your target persona
  • How those pains and the cost of in action impact your target persona and key stakeholders. 
  • How they prevent your target persona from meeting professional and organizational objectives.  
  • Which emotions are triggered by all of the above and why.


By the time team members complete the process, they’ll be able to better articulate what problems you solve for who – in simple English. 

The comfort they’ll gain will give them receive a confidence boost enabling them to have easier, more meaningful conversations

TrustArc CRO Jason Wesbecher shares how CWFRT helped his new reps ramp quickly


led to:

Reduced ramp time

TrustArc's CRO attests that after completing a workshop, TrustArc's new sales hires were able to express what problems they solved for who - in simple English - before they started on the job.

Team attained 103% of quota. The ASP on new business increased 92% in the quarter post-workshop.

How this helps your team's:

Prospecting & Cold Outreach

Comedians (who aren’t household names) have a short window to make their audience laugh. If they can’t do it, audiences tune out.  

Prospects are no different. They’re bombarded with cold outreach across multiple channels.  

Most of it’s more templated than a CEO’s post-layoff apology, making it harder than ever to start conversations.  

Pipeline generation efforts need hooks that shine a light on the problems your organization can eliminate for your prospects.

Much like in comedy, the right opener in outbound prospecting & social selling earns attention, demonstrates credibility and builds trust – all in 5-10 seconds.  

Icebreakers can come from my workshops or “Humor-as-a-Service”.

Let’s adapt & repurpose the best ones for use across multiple outbound and social channels and even coach your team on how to exploit them, so they can start more conversations with prospects…

…and less with your leadership.

The only thing colder than your outreach...
...is the shoulder prospects give it.

Memorable, relevant messaging

led to:

Revenue from cold email

TrustArc generated net new revenue using cold emails anchored by bespoke icebreakers.

How this helps your team's:

Content Creation

Need memes? Carousels? Short-form video? Linkedin hooks? 

Your team’s – or my – creative output can be adapted to any or all of the above – and so many other types of content (including video).

Icebreakers can come from my workshops or “Humor-as-a-Service”.


Memorable, relevant messaging

led to:

Personal branding

Jon crafted icebreakers specifically to help Broadcom product evangelist Jeremy Rossbach raise his profile in the Network Operations Management community.

He saw an uptick in followers from humor being converted to posts injecting it into presentations and conferences, and in podcast guest appearances.

How this helps your team's:

Trade Show Engagement

When prospects approach a booth of a company they’ve never heard of at a trade show, staff have mere seconds to educate visitors as to their company’s “why”. 

Yet many hope and pray that their bland, buzzword-laden pitches tell the story – which they can’t.

Companies often invest in:

  • The trade show booth
  • The booth display 
  • Printed collateral
  • A giveaway prize
  • Transport feels for all of the above
  • Flying, housing, and feeding staff…
…only to not prep staff to properly engage prospects.

The right opener helps booth staff engage, stand-out, be relevant, break the ice, and have easier, more meaningful conversations.

Powerchord is a SMB SaaS company, who generated $160K in net new revenue (in 2 months) from convos started at trade shows using funny, hyper-relevant icebreakers I crafted for them.  Watch CRO John Crosby’s testimonial

Powerchord CRO John Crosby's team attributes success from trade shows to "Humor-as-a-Service"

Memorable, relevant messaging

led to:

Trade show engagement

Powerchord generated $160K in net new revenue from convos started at trade shows using funny, hyper-relevant icebreakers I crafted for them - in just 2 months.

How this helps your team's:

Team building & boring onsites

Bringing team members together for an onsite (or virtual) meeting and not having them:

  • Share tribal knowledge with each other
  • Get creative
  • Align with one another
  • Learn new skills
  • Get out of their comfort zone
  • Laugh
  • Have some fun… 


…is a missed opportunity.

Learning & development happen when it’s experiential and fun.

Combine an entertaining, insightful, user-friendly keynote from a guy who’s met quotas of sales and laughs…

…with a team-building workshop that gets your team sharing tribal knowledge, and learning a creative, practical approach to engaging prospects.

Add in some post-onsite coaching hours to help reps deploy their learnings for maximum impact.


Scenes from an onsite workshop:

Ask about virtual or hybrid workshops.

How this helps your team's:

Sales & Marketing Alignment

“This call/email/Linkedin connection request’s colder than the relationship between sales and marketing” 

That joke crushes when I use it to prospect sales and marketing leaders because it highlights the silos that the work in.

The two need to work in tandem to grow revenue, but often operate like competing interests.

My workshops force sellers and marketers to join forces and share their knowledge, insight, perspective, and creativity with one another, and get on the same page.


Neo4j sales leader Rick van Bruggen:

About Jon Selig

“My 12 years in stand-up was a well-paid internship for my career in stand-up comedy.”

Jon received his BComm & MBA, and spent time in business process consulting, followed by a 12 year career selling ERP, business intelligence, and professional services (for both Oracle & an Oracle partner – he still can’t tell you what a database is).

In 2011, his career took a sharp left-turn and he started performing stand-up comedy in hopes of fulfilling his lifelong dream – of never selling technology again.

Jon found the parallels between sales and stand-up to be so striking, he felt sellers could benefit from the skills, methods, and processes that both practitioners share.

After years of performing at clubs, festivals, and forecast meetings, he created Comedy Writing for Revenue Team.

To date, he’s spoken to and worked with teams at Broadcom, TrustArc, PowerChord, Canon USA, Citrix, Zoho, Philips Healthcare, InfoBlox, Microsoft Canada, Fleetcor Technologies, and more.