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 there, and not because I was the only 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-coning technology, I won’t be working in a modern sales organization any time soon. I couldn’t add a lot to many of the topics being discussed, because of my situation.

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 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. It took some time, but I backed away from the “post-connect pitch” and began sharing my knowledge with my network, by creating 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 in a way that isn’t time-consuming 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.

Part I: Peer Learning Learnings

The following blog post is a series of exaggerated truths and embellishments.  It’s part 1 of 2.

Since I’ve been a kid, I’ve been fascinated (and occasionally repelled) by nerd culture. I used to be all-in on comics & sport card collecting. I’d track down every book & newspaper article that covered this super-important stuff, devour them, cut them out, and put them on my bulletin board. I had no time for friends or family, as my passion was consuming me. Then I turned nine. 

Fast-forward years later, I became fascinated by the ins and outs of stand-up comedy, and mastering it (not a thing). I read blogs, joined Facebook groups, and yakked with fellow wannabes at wherever I did open mic & shows.

Today, sales culture has entered the realm of nerdery. It’s so navel-gazey, we see lint. Young SaaS-y sales pros hanging out on LinkedIn to glean new knowledge, show older mavens their stuff, and work on their brand. Most importantly, they’re there soaking in the glamorous world cold emails, discovery calls and - of course - how to do the “HGC” (hustle, grind, and crush).  

Another perk of being a sales nerd is the incredible meet-ups and conferences for sales practitioners and leaders. These valuable resources are there if you want to enhance your sales game - and great news - your company could even to cover the costs. 

Understanding such value, I recently vacationed at a sales conference. May sound weird at first glance, but why not? I felt like I was going to an all-inclusive - it was held at a resort, had fantastic, all-you-can eat buffets, and everyone was drinking up the dark roast coffee, fruity juices, and impactful sales learnings. 

While there, a fellow attendee started a conversation with me. and told me he was a sales development manager. I told him I help sales teams learn how to find funny in their prospect’s world. 

“Cool!” he proclaimed, and then suggested that I join “The Secret Society of Sales Superstars”.  

“Sure. What’s that?”

“Yeah…um…it’s a thing you should… really check out. Yeah.”

As he said that last part, he delivered an intense look, like one delivered by a mafia don who has a stranglehold on the “sound career advice” market.

“I mean, ok…but…can you elaborate?”

“Sure. But what part of that look I gave you a minute ago was unclear?” he said sternly.

“Oh, it’s fine. I get it, Guy-I-Just-Met-in-a-Hotel-Restroom”.

 Turns out SSSS is a closed community for serious sales practitioners who want to learn from one another’s success (& failure) and it just so happened one of their infamous meet ups was happening while I was in San Francisco.

The event unfolded as follows:

Registered sales practitioners register check-in, and proceed to pile savoury middle eastern foods onto their plates, and sit at a round table. The meats, veggies and hoppy beverages induce attendees’ sales wisdom & opinions on best practices on an assigned topic, and each topic is part of a larger theme of the evening.  Each table is assigned a moderator. A topic related to modern sales is presented, and moderators prompt everyone at their table to offer some their insights.

Some insight I quickly gleaned, is that there’s no better way of realizing how detached you are from the minutia of sales, than to listen to sales leaders talk about it.

The first question was (roughly) “Which metrics are of increased importance?"

Sally, a Director of Business Development answered:

“I don’t care what channel my SDRs use to reach prospects, as long as they’re booking meetings.  We measure activities - calls, emails, SMS, etc.”.

Everyone nodded in agreement.  Next up, was Steve, a Regional Manager at a SaaS.

“We measure metrics that measure enhanced metrification”.

“Us too!” said a delighted Mildred, while everyone else nodded. I also agreed, because fitting-in is fun.

It was then my turn to share my thoughts. Everyone’s eyes were thrust on me. I made two things clear: a) my kitchen table doubles as my office, and b) my key metric is “airplane tickets booked” - in that if I none, I will have to call myself into a back room to let myself go.

Everyone smiled, but these people want actionable intelligence - not comedic brilliance.

I’m a comedian who helps sales teams better understand their prospects, and relate to them so they can start more and have better conversations, and who promotes himself on LinkedIn. You have a day job, which means if you don’t start getting going on your day’s activities, you may end up having a talk with your boss and I don’t want that.

Which is why you need to return for part 2. All joking aside, I learn a ton from sales practitioners and managers at sales meetups whenever I shut up and open my ears.

I can even contribute occasionally, as I see things through a bit of a different lens. I actually shared some important wisdom about LinkedIn’s role in the sales process, and how it can be measured and justified as a place to spend a greater portion of your day than your managers would imagine. I’ll share it next time. Admit it - you love a good cliffhanger.

To be continued…

Einstein, Allen, and Tommy Boy

Since I began offering what amounts to be a “comedy writing for salespeople” training & workshop, people react to what I offer the same way they do to a new Star Wars trailer: thrilled and confused. In short, I want sales reps to simultaneously obtain their prospects' attention, and show a grasp of their challenges.  Let’s kick things off with a quote:

“Insanity is doing the same thing over and over again and expecting different results”  -Albert Einstein


If Einstein was around today, his LinkedIn profile’s tagline would read “Influential Thought Leader In Stuff You Don’t Understand”.  However I disagree with Einstein, as I’d change “insanity” in the above quote with “stupidity”. Though, in his defense, he invented a theory of relativity, while I struggle to score likes & shares on LinkedIn. If he was around today, he’d have reverse-engineered LinkedIn’s algorithm while trimming his moustache and be in fact a leading influencer. The irony is that the solution to my own problem is to post something antagonistic on LinkedIn like “Me: Smarter than Einstein. Fo’ Realz, YO!” (nothing like sowing the seeds of outrage to drive interest in your own brand, but I digress).

So many potentially fruitful businesses or ideas within businesses are burned to the ground because of incompetence, greed, ego, and a lack self-awareness. So much innovative thought & morale are tossed into metaphorical bonfires because leadership doesn’t have the will or desire to fix basic problems. So, it’s hilarious when leaders make the same mistakes over and over again. Except when they’re our bosses.  Then it’s tragic.

“Comedy = tragedy + time” - Steve Allen



This equation is far more meaningful to me than anything that know-it-all Einstein ever proved. Back in 1937, Hindenburg jokes were taboo, but today, it’s a metaphor for disaster. Yet, in the business world, struggling through hard times just to someday laugh about them is neither a payoff nor an option.  Repeated insanity experienced by employees in the present, is an utter tragedy, which not only affects profitability, but also diffuses morale and lower productivity. Ominous stuff. Nothing says “hilariously good times” like mass layoffs.

Good salespeople are like psychiatrists. We let prospects traumatized by operational frustrations vent their problems in a forum we offer them.  Our role is to listen and prescribe the right medication to cure the patient, and get them back to a healthy operational state.  That said, the first step in asking for help, is knowing it’s needed. Part of our role is to help our prospect admit (or see) that they need to open up to us. To do that, we need to:

1)    Get their attention;

2)    Display empathy;

3)    Be respected & liked.

On the other hand, stand-up comedians are the ultimate attention-getters.  We seek buy-in from their audience because we speak about relatable challenges/observations, and frame them in a way that drives engagement. And like the comedian, sales reps need to achieve this quickly. Attention spans are shorter than ever. Whether it’s on a cold call, or during a demo/sales pitch, a well-crafted, well-placed joke can do it all in a couple of short sentences.  

Consider the following, which I crafted for an employee at a company that sells pre-built predictive analytics tools to clothing retailers – everyday, comedic fodder.  Test yourself, and deliver it out loud. Imagine you’re onstage and need to project, and deliver with some charisma:

Clothing retailers are building their own predictive analytics tools in order to make more informed decisions, but building software is not core business. That’d be like if Oracle opened a “Big and Tall” shop. 

I know, I know: too soon. This joke will not be appreciated by everyone, but it doesn’t care. It wasn’t written for comedy club or my Netflix special.  It’s for a very specific audience – the vendor’s prospects. Helping prospects laugh about their problem can become their first step in fixing it.  Such jokes show the prospect that the rep understands a challenge they face, their industry, and it should get the prospect to – at the very least – crack a smile and crawl onto the couch for deep therapy. 

If you're in Montreal, check out my therapy most Sundays at my weekly stand-up show in Montreal:

Austin: America's Montreal

My top new year’s resolution was to write a weekly blog post about the crossover between stand-up and sales - without fail.  I was determined to stick to a schedule, and I initially attacked this the way a keener SDR does their 100 required daily dials. “Initially” means 2 weeks of blogging, before being derailed by everything else associated with being a digitally-driven entrepreneur. Blogging had to take a backseat to my planning for last week's trip to Austin, and a re-watch several Sopranos episodes.  

That said, I’ve reconciled this with myself (as the undisciplined repeatedly tend to do).  My rationale is that I’d rather post worthwhile stuff intermittently, instead of a steady stream of mediocrity.  Great art isn't crafted on a schedule. That said, this isn't great art, but I strive to write something enjoyable about the intersectionality of sales & comedy, and/or my career speaking on it.  And, sure, that orange, goopy cheese is tasty, but I’d rather have weekly tacos vs. daily nachos (unless the tacos are vegan). 

There are parallels aplenty between Austin and my hometown of Montreal.  Both cities play host to giant music festivals, an annual Formula One race, fatty foods, craft beer, artistic communities, startup culture, and both cities that know they’re distinct from the rest of their state/province, which believes it’s distinct from the rest of the country.  If Montreal was a Starbucks beverage, it’d be named “A French, Cold Austin”. If Austin was a cult movie, it’d be called “Hot, Wet, American Montreal”.  

While in town, I presented an abridged version of my training & workshop to the local chapter meetup of the American Association of Internet Sales Professionals (AA-ISP).  Chapter President and all-around swell guy Gary Smyth, who I had collaborated with in a past life.  If you’re looking for a fun new way to spend a lunch-hour I recommend playing  “3 Degrees of Gary Smyth” with others in the Austin tech world. Forgive me for referencing a cult Canadian television show, but Gary Smyth is to 2018 Austin tech world what this guy was to 1970s Toronto. 

Thanks to those who attended (close to 30 in the room!), especially those who participated in the collaborative joke-writing exercise.  Lucky readers of this post will soon be converted to lucky viewers, when they check out some of the collective output, as delivered by some sales enthusiasts & startup founders in a forthcoming video!

I was excited to meet the local sales community, and un-Canadian weather in January, but was even most excited by how a local restaurant celebrated my arrival in Austin:

I fulfilled a lifelong dream of performing stand-up comedy outdoors in January. Thankfully, it wasn’t in Canada.  Chris Collings runs a really fun showcase monthly at The Vortex Theatre. 

Austin's become a favorite destination of mine. It's the right mix of business, art, and deliciousness. It's not too big, it's manageable, and everyone's so damn Canadianly polite. And for those of you keeping score, Tacos prevailed over BBQ in the "Austin Mealtime Challenge" 4 means to 2.

Broken resolution #2: To blog on stand-ups’ annual planning, and set quotas for themselves before Jan 29th, 2018. Until next time.