“Comedy Writing for Sales Teams” in 1 Minute

Knowing your audience. Getting prospects’ attention. Getting them to open up. Seeming human to them. Communicating value.

These aren’t jokes, just things sales & sales development reps struggle with.

This 1-minute explainer video shows how “Comedy Writing for Sales Teams” helps sales reps tackle all of them.

A well-crafted, repeatable, hyper-specific joke about the pain you solve for your prospects enables more, better conversations.

If you like this video and think you or your team could benefit, please share this page with your senior leadership, the folks that are organizing your 2020 Sales Kickoff, and/or who evaluate sales training and team-building.

If you are one of these people, feel feel to find a convenient time to speak by clicking that blue button below. I’d love to help your team start more & have better conversations.

Want to go deeper? Plunge into my Virtual 1-Pager.

The ROI of What I Do

The unofficial name of my workshop is “Comedy Writing For Sales Teams”, and it sets the expectation that I’m always hilarious.

True fact. As I write this, my assistant is about to unknowingly sit on a whoopie cushion I placed on his chair.

The goals of my workshop are to help sales teams create statements which demonstrate their - and your company’s - credibility and make them memorable.

Often enough, I’m gruffly asked “What’s the ROI of what you do???”.

To be frank - no clue. None of my initial clients are currently measuring any of this, and no one’s developed an app to measure personality and human engagement.

The first two years of my practice were all about showing sales teams how comedy writing process builds subject matter understanding, and how both it and the jokes which come out of it can help sales reps show prospects they understand the problems they face, their impacts, and how they can solve those problems.

However, I have a couple of stock jokes which have helped me connect with 2900 LinkedIn contacts, kick off countless cold call conversations. Some of those calls converted into my clients. Seems clear to me.

(PS: Odds are if we connected on LinkedIn, I used one of them on you! Review our correspondence, and if you don’t recognize it, drop me a line and I’ll send it over to you).

One of those clients was Ryerson University’s DMZ, a Toronto tech accelerator (put your hack military joke away).

I spent a day helping six startup founders “punch up” their pitches, and DMZ Sr. Director Hussam Ayyad vouched for what I do & how I do it in a video testimonial.

It’s the last video on my testimonials page.

That said, as Comedy Writing for Sales Teams (aka “Funny Enough”) heads into its third year, I’m looking to implement more meaningful programs that ensure that SDRs & AEs can effectively deploy humor to start conversations, have better ones, and that where possible, the results can be tracked. Cold outreach is an easy spot. Get in touch if you think it could uplift your team’s results.

Know Thy Audience

Account Executives, SDRs & Customer Success must all relate to their audience, and come off as human as opposed to random titles like “soulless dialling & emailing machine”.

"Show 'em you know 'em", we're told.

I'm a big believer in starting conversations with prospects by showing understanding of their challenges, while being memorable. This is super important in both sales, as well as stand-up comedy (who knew I’d make that parallel???).

This summer, I had the honor of being booked to perform at a fundraiser for the Canadian Hard of Hearing Association. My first instinct was "I'm being asked to tell jokes to people who can't hear. How well can this go???".

Bad assumption. I’d found out the DAY BEFORE that the show was billed as Montreal’s “first-ever, fully accessible standup comedy event”. The comedians’ jokes were communicated via closed captioning, T-loop (a special type of sound system for those with hearing aids), sighted guides and ASL (American Sign Language) interpretation.

With this knowledge, I felt covered. I wanted to deliver a joke very early in my set which I felt the crowd of over 250 people could relate to. I wanted them - and every audience I perform for - to like me. Being liked helps build trust and empowers me to take my audience to places I perhaps otherwise couldn’t.

I ran it by the organizers to see if it was a) funny, and b) crossed any lines. I was told I was in the clear. Here it is:

For stand-up comics that aren’t household names (99.99% of us) our audiences are both clients (they’ve paid) but also prospects. We want them to follow us on social media, subscribe to our newsletters, check out our content. If we can’t relate & connect, someone else will, and we’re forgotten.

This joke helped me connect with the crowd. Once I did, I had their attention and they had “bought into” me. The rest of my set went really well, and I earned my fifty bucks.

The morals of this story are:

1) Show your prospect you know who they are, and what their struggles are.

2) Do it early.

3) Be memorable.

4) Sales pays better - MUCH better - than stand-up comedy.

Part II: Peer Learning Learnings

In part I of this blog, I discussed a sales meetup I attended in San Francisco that was predicated on roundtable discussion/peer learning, networking, and savoury foods.

I felt out of place, and not just because I was the only one using my IPA as a dip for my chicken shawarma. I was an outlier at the table. Everyone else was part of or leading a team of sales pros. I was the sole solopreneur, and until I raise my Series A and invest in self-cloning technology, I won’t be working in a modern sales organization any time soon. As a result, I couldn’t add much to many of the topics being discussed.

Things changed when a new topic arose, and someone at my table began discussing the various channels her reps use and what metrics define success for each one. When the manager listed “social selling”, the whole table wholeheartedly agreed that it has value - but that because social selling activities couldn’t be tracked, its value couldn’t be measured and proven.

This triggered something and the gears in my mind started turning. The squeaking gave me a headache. My mind traveled back in time to view the way I used to do things when I was a quota-carrying sales rep. LinkedIn’s purpose at that time, was there to help me identify which IT execs to cold call (I sold enterprise tech), update my work experience, and accept connection requests from old colleagues who I didn’t like.

Like any entrepreneur from the pre-data analysis era, I don’t need no stinkin’ data to tell me what to do. I run my business on gut instinct (which is a braggadocios way of saying “I don’t know how to measure any of that”), but my gut told me that LinkedIn is the channel where I need to spend a lot of my time. Unfortunately, when I launched “Comedy Writing for Sales Teams”, the way salespeople were using LinkedIn had really evolved - and I never got the Slack message.

My old LinkedIn persona was a composite of Ron Burgundy and “Ol’ Gil” from the Simpsons. I was the perfect example of that guy that every sales influencer rages about “STOP PITCHING! BUILD RELATIONSHIPS THROUGH VALUE! AVOID SELF-INDUCED HEART ATTACKS!”. I was making things about myself. I didn’t try to get to know my connections or offer them anything (except my all-around amazingness). I just assumed they were on LinkedIn to accept my life-changing insights & offers.

I couldn’t have been more far off. I quickly eschewed the the “post-connect pitch” and began sharing my knowledge with my network, creating & sharing video content, pumping out articles, participating in discussions, and cultivating online relationships, which then turned into offline ones.

After breaking into a cold sweat because of these memories, I realized where I was, and that I had a contribution to make. I dunked one last morsel of chicken in my beer, swallowed and sprung into action.

I explained to my table-mates, that as a solopreneur, I need to be my own sales & marketing teams, admin, and top to things off - I’m the product and service provider.  When it comes to sales, I create my own content, create & run my own drip campaigns, and make cold & warm calls.  My particular circumstances also mandate me to spend a lot of my day on LinkedIn. If not for it, I couldn’t be building my business. 

I declared exactly that, and started to spout out all the ways in which LinkedIn helps me grow my brand, drives engagement - all of which COULD be tracked if I had the time & means. These include:

1) New connections, gained from: 

  • Those who interact and appreciate my content;

  • Requests I proactively send out;

  • Those who have seen me speak, or taken one of my workshops;

  • Those I met at industry or networking events.


2) Conversations Generated:

From those conversations, how many:

  • Opt-in emails can I gather?

  • Phone numbers can I gather (publicly listed, solicited, or - gasp - scraped)?

  • How many conversations can that information generate?

  • How many meetings can I book?

  • How many of those meetings turn into opportunities

  • Intros made by your 1st degree connections

  • Activities taken on Linkedin per deal

  • Which pieces of content put out which yield the most connection requests because your expertise or knowledge is appreciated.

  • Offline conversations generated from LinkedIn interactions.

Sure, tracking all of the above is a challenge, but it’s not hard to guesstimate many of these. Phone, email, or social selling are all separate channels which need to be mastered. Sales teams invest heavily in measuring how well the first two are being used, but don’t in the latter. 

My words were well-received. After doling out this advice, a silence fell over the table. Peoples mouths dropped, before they stood and applauded. A tear even streamed down the cheek of one VP of sales. I was honored and validated.

Sure, that last part’s completely fabricated, but admit it - you like blog posts with formulaic Hollywood endings.

Jon Selig spent 12 years selling enterprise technology, which was a well-paid internship for his career in stand-up comedy. Jon shows sales teams why & how to craft humor that roasts prospects’ pains, starts more conversations, and helps reps keep their day job.