A Very Serious Offer

Better engage prospects, convert more leads, and upskill your team

Use me as a fractional resource to support and enhance your current go-to-market efforts. This includes:

PowerChord CRO John Crosby was seeking new ways for his team to connect at trade shows, and through cold outreach:

Why do this?

Get prospects to know, like, and trust your people and brand

  • Give your team a framework to help your teams better understand what problems you solve for who, how they impact your prospects, and how you solve them
  • Help ramp new hires quicker
  • Upskill new & tenured hires’ written and verbal communication
  • Harness and tap into your team’s collective knowledge, creativity, and desire to be part of an important process – message creation
  • Boost confidence
  • Give your team a framework to help your teams better understand what problems you solve for who, how they impact your prospects, and how you solve them
  • Help ramp new hires quicker
  • Upskill new & tenured hires’ written and verbal communication
  • Harness and tap into your team’s collective knowledge, creativity, and desire to be part of an important process – message creation
  • Boost confidence
  • Top-of-funnel success via memorable, customer-centric messages. How?
  • They earn prospects’ attention across sales & market channels, and help your start more conversations. How?
  • They show deep understanding of prospects’ challenges and paint powerful pictures about why they should care about you.
  • They’ll help your team better connect with prospects via cold outreach, trade shows, social selling, content creation, and more (scroll down).
  • Each icebreaker anchors fresh content multiple creation efforts.
  • Let’s work together in a sustained – vs. one-off – fashion, to drive results.


Past successes:

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.

Revenue from cold email

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

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.


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.

Choose what you need:

Where does your go-to-market team need help?
Pick & choose what you need based on your unique needs:

Hook more prospects

I'll interview internal stakeholders to capture who your audience is and why they should care about you.

I'll then craft 20-30 icebreakers that highlight points you wish to impress upon prospects.

Review examples!

Trainings. Team-building workshops. Kickoffs. Team meetings.

Build your team's understanding of your prospects & why you matter to them with "CrossFit for seller communication skills".

Develop. Ramp. Align.

Give your team an opportunity to share tribal knowledge, boost understanding of prospects, and written & verbal communication skills.

Onboard new hires faster.

Better align go-to-market teams.

Learn a creative process that can help better connect.

View 18 takeaways from workshops.

Strategy and deployment

I'll adapt icebreakers to outreach and content that can reach your prospects

ID where prospects are & how to adapt messaging

We'll work together to map out how & where your prospects can be reached, and adapt the message accordingly to ensure they "get the message".


To help sellers and marketers use icebreakers and content to better stand out and connect with prospects 

Let's work to improve

I'll coach them your team to exploit messages, create their own impactful messages across channels of reaching your prospects.

Can be delivered one-on-one or as a group where all learn together from best practices and what's working.

Use cases for icebreakers:

Cold outreach

Adapt each icebreaker for:

Written channels:     • Cold email • Linkedin connection requests • Linkedin DMs • SMS

Verbal delivery • Cold call scripts • Voicemails • Linkedin voicenotes • Video engagement

Trade show engagement

Drive traffic, engage visitors

I can coach your staff to engage icebreakers with hyper-relevant humor...OR....

...I can be part of your booth in order to drive traffic and better engage visitors

Content creation

A library of shareable assets that POP!

Use humor to create content (video, text, image-based, etc.) that earns attention and educates on social platforms and beyond

Social selling

Stand out in cold outreach!

We'll transform each icebreaker into a series of "plays" (written posts, animated GIFs, recorded videos, memes, and more), arming your reps with steady content to share over time to educate prospects on Linkedin or other platforms.

Pre-sales / demos

More engaging, entertaining demos

Arm your pre-sales team with humor to inject into demos that make powerful points, and re-set prospects' attention spans. 

Leadership & Presentations

Improve public speaking impact

One or 2 bits of relevant humor can help an executive make memorable points and leave a lasting impression when speaking or presenting to investors, at a conference or to their entire team.

How we'll work together:

Step 1: Objectives & Needs Assessment

- 2 key business points (i.e. a problem you solve, an impact of not solving it, how you'll solve it, or what makes you different) you wish to impress upon
- 1 audience (a target persona, defined role).

We'll discuss where your prospects can be reached (which digital and real-world channels) to determine how we deploy the humor once created.

Step 2: Discovery

Hyper-relevant humor isn't possible without having a requisite understanding of your "So what?" and "Who cares?".
I'll run several hours of discovery sessions with your internal subject matter experts and document their answers to 23 questions. We need to unearth what's painfully true to those you're trying to influence and flesh out how they and their key stakeholders are impacted.

Step 3: Crafting Some Funny

I'll craft 20-30 icebreakers (short-form humor) written to impress key points you wish to impress upon the prospects you want to connect with.

I'll run them by you (and/or your team). Some will hit, some won't. Gotta break a few eggs, right? Omelettes are worth it.

Head over to the next step to learn what we'll do with those that hit.

Step 4: Deployment

Once you have some humor that target prospects appreciate, we'll collaborate on a plan to earn their attention and build your credibility as subject matter experts.

There's 15 ways to go about it. Let's discuss what's best for your objectives.

Step 5: Coaching

Once we've adapted your icebreakers to your desired channels/prospect touchpoints, we'll evaluate what is and isn't connecting with prospects, why, how, when and where.

Once we better understand, I'll work one-on-one with team members or in a collaborative group setting to help improve their cold calling and other outreach efforts, social selling/Linkedin presence, trade show delivery, content creation, value articulation, presentation skills, and more.

Communication skills, knowledge, and creativity for your team

Parallel to helping you get the message out there, let's empower your team to better understand why your prospects should care about you and delivering it.

Master your Value Prop

"What problems do we solve for who?"

We can't craft something funny unless we understand a) what's hurting our prospect, and b) how they're impacted by pain(s) we can eliminate for them.

Create & craft memorable messaging

Structuring insights

"Jokewriting 101 for B2B" will teach relevance, brevity, and memorability.

Delivery, communication skills, confidence

Written & verbal communication

Participants will be taught new ways to express their value proposition and leverage their messaging across multiple channels and touchpoints.

What's the deal?

Not ready for this type of arrangement?

Start smaller with Humor-as-a-Service or Trainings & Workshops

Let's discuss your needs: