The Writer's Room

Team up with a few.
Benefit your whole team.

A monthly live class that enables 3-5 team members to combine knowledge & creativity to craft messaging that paints pictures, stands out, and helps the rest of your team start more and have easier conversations.
“Comedy writing is collaborative, in the same way that tug-of-war is collaborative. It’s not that one person can’t do it; it’s just that [several] do it better and more easily.”  



Standing out in prospecting efforts. 

Cold  outreach needs to: – Speak to your buyer’s needs and objectives  –  Stand-out from the ho-hum – Elicit an emotional reaction from them. 

Fostering and enabling creativity.

A single seller or marketer can rarely craft messaging that’s both relevant AND memorable.

Onboarding new team members

Getting new SDRs, AEs, and CSRs  to quickly articulate what problems you solve and for who – in simple English.

Lack of leadership consensus 

Early stage leadership isn’t always on the same page about who their solution helps and why.


Your favorite TV or movie comedy wasn’t written by one person, but pooled the creativity of 6-12 people.  The Beatles couldn’t create as well as solo artists as they could as a team. Heck, I bet you sometimes  want extra help in the kitchen.

This monthly live Class will teach a group (3-5) of your subject-matter experts & creative team members tools and a process to create openers to help them (and the rest of your team) break through the noise, start more conversations, and keep their day jobs. 

What You’ll Do

Team Members will Collaboratively:
Build out full portraits of your key buyer personas including:
  • Their role
  • Their desired end-state
  • Their most common struggles
  • How they’re measured
  • What success and failure look like
  • Their emotional trigger points
Dig deeper into the problems you solve
  • The impacts of not solving them
  • Which other stakeholders are affected

What You’ll Get

  • A step-by-step process to transform all that stuff above into openers that roast your buyer’s pain
  • Peer learning & collaboration
  • A deeper understanding of your buyers and why your company matters to them
  • An opportunity to exercise creative muscles
  • New ways to improve your phrasing and expression…
  • …and finally break free from the evil Buzz Wordington
  • Consensus
  • An opportunity to take my full training & workshop for a test drive.

12 Outcomes from Crafting Humor as a Group

The process of writing and testing jokes forces us to:

1) Define who our audience is

2) Articulate why we matter to them

3) Understand their goals & emotions

4) Break down why & how our offerings can affect them

5) Write/express ourselves around them

6) Master language (and ditch jibberish-y buzzwords)

7) Rephrase them

8) Break-down concepts

9) Present/speak in public

10) Get creative

11) Loosen up

12) Create memorable ways to connect with your prospects.

Add-On Options:

Jon Writes Jokes

I’ll write 10-15 jokes to illuminate up to 3 specific points you want to impress upon your prospects.

Playbook Creation

I’ll adapt up to 5 jokes for cold emails, LinkedIn connection requests, voicemail/video & cold calls (where applicable). Share the playbook with your entire team.


I’ll walk your entire team through the playbook, and teaching them how to deploy it. We’ll role play, practice, and fail publicly – so reps can succeed IRL.

Upcoming Workshops:

How ONE joke can open door after door...


  • Memorable messaging. Assemble & register a “Tiger Team” of creative people who really understand your company’s value
  • Senior leadership alignment. Are you all on the same page about your company’s “So What?” and “Who Cares”? This class will align y’all.
  • Onboarding new sellers. Have a few new hires? Team them up with a savvy, veteran teammate or two. When it’s over, they’ll be able to express what problems you solve for who (in simple English), and have more confidence to deal with prospects and customers.
  • General upskilling for top performers. A-Players want to keep growing. Give them another arrow for their quiver.


  • Register a group of up to 5 (not limited to sellers or marketers)
  • Jon will facilitate pre-work over a 1 hour private session, followed by:
  • 4 x 2 hour sessions
  • This is an “open registration” class, with a maximum of 5 groups per class
  • Upon completion, Jon will “Punch-Up” and edit each group’s jokes
  • Add-Ons can be…um….added on….for a more robust final deliverable


A CRO's testimonial

Many sales reps testifiying. A "testi-montage" if you will