Comedy writing can be a secret weapon for revenue teams who want to be more engaging. In this episode, Mark Cox welcomes stand-up comedian Jon Selig, who created Comedy Writing for Revenue Teams, to share his secrets to using humor effectively. Jon, a former enterprise tech salesperson turned comedian, reveals the surprising parallels between stand-up and sales and how laughter builds trust and drives revenue. Learn how comedy writing helps craft relevant messages that resonate with your audience, focusing on preparation, timing, and punchy delivery. Tune in and transform your sales and marketing with the power of laughter.
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Comedy Writing For Revenue Teams: How To Engage, Connect, And Convert With Jon Selig
Is there a place for comedy and professional sales? If you've listened to a few of these podcasts, you'd certainly understand that comedy has been a big part of my life professionally and personally. When I think back to some of the best relationships I've got, they started with this love of comedy where it's my older brother or friends that I went to university with. We were insane fans of Monty Python and SCTV. In later years at times, even something like Saturday Night Live, just love this idea of laughing.
I'm really excited for our conversation because we're talking about this alignment between comedy or stand-up comedy and professional sales. We found somebody who's got just such a unique niche in this space. It's Jon Selig. Jon is the founder and chief of staff in Comedy Writing for Revenue Teams. It's a sales training consultancy. Help go-to-market professionals leverage skills, processes, and methods of stand-up comedians to transform them into more consultative sellers and stronger communicators, help them use storytelling, and then arm them with impactful messaging for top-of-the-funnel efforts and beyond.
It's really interesting when we start to get into the alignment between comedy and sales. First of all, we start with the idea that they're both performance arts. When you start, it takes a lot of courage to get up there and do that. There's a way of creating connections. Comedy is a great way of creating connections and building authentic human relationships. Frankly, there are some tactical things in handling rejection and sometimes failure with humor. I do think there are these more strategic, positive things like in stand-up comedy, you really need to know your audience.
The Journey From Enterprise Sales Expert To Comedy And Sales
You've got to engage them quickly. You've got a personalized message. You've got to break down complex ideas into simple jokes. Think of all of those things I just said. Of course, they're all so applicable in B2B sales today, which is this niche that Jon teaches on, which is so smart in my view. This is just a great conversation. Obviously, it went in a flash for me having this conversation. Jon has a background as an enterprise sales rep with Oracle doing multiple different roles for many different years.
He really does understand that world. He jumped into this world of comedy as an adult. That talk about a creative sleep there. I think you're really going to enjoy the show. I did for sure. As always team, two things, please like and subscribe to the Selling Well podcast because that really matters to us. That's actually how we get really good guests like Jon. Also, share your constructive criticism.
If there are ways that we can make this show more effective for you, that's what we want to do. We're really trying to create an MBA in professional sales here with this body of work on the podcast. Drop me a note at MarkCox@InTheFunnel.com, or connect with me on LinkedIn and let me know your thoughts. We love constructive criticism and we respond to every note we get. Team, here's Jon Selig.
Jon, welcome to the show. It's so great to have you.
Thank you for having me. It's a pleasure to be in my own apartment.
Listen, I was really excited. This was a red-letter day for us for a couple of reasons. Like most people, I think I'm funny. At this stage of my life, by the way, I also inject just a ton of humor into almost every aspect of life, where it's appropriate and where it's not appropriate. This topic of comedy and sales, I've heard you on other people's podcasts, and I just think it's such an interesting topic. It's also really interesting to me for a lot of reasons, I think the bravest people in the world are stand-up comedians who get up in front of a mic and try and make a room full of strangers laughing, all those good things. First of all, welcome to the show. I'm super excited to have you.
I'm super excited to be here. Thank you for having me. I would not say that stand-up comedy takes bravery whatsoever. It just takes a lack of dignity.
There you go.
People say that, “You're so brave.” I'm like, “I don't know. I just have a little bit less shame than a lot of people.” I don't know if that constitutes bravery, but I'll let you believe that if that's what you want to believe.
Let's go with the bravery thing. I think it looks better for you. It's also better for the show notes. By the way, as I was rushing here to get onto the podcast, one of my favorite podcasts is Fly on the Wall. I don't know if you listen to that.
I do.
With David Spade and Dana Carvey talking about some of the experiences of Saturday Night Live, and it's just amazing to me. Again, the bravery, the courage, because many of the best performers, there's only been about 450 people ever who have been performers on Saturday Night Live. Like over the 50 years, it's really not that big a group. Many of them suffered just paralyzing stage fright, where they'd be having these breakdowns before the show, like some of the best ones.
Dana Carvey was one of them, by the way, for a long period of time. It's just really interesting to me this whole topic. Tell us the short story of your journey. I know you're an enterprise sales expert. How does somebody who's enterprise sales deep experience end up talking about this topic of comedy and sales?
Mainly because I didn't want to sell enterprise technology after doing it for about ten years, but that's a bit of an exaggeration actually. I was selling Oracle, enterprise, business applications like Oracle ERP and they're all the associated business software with that and selling professional services doing really full cycle sales for the better part of ten years, calling, running in deals from the inside and going to the outside where necessary to get deals done.
Whatever it takes, both for Oracle itself and then for an Oracle consulting partner. I hit a wall with everything and I started performing stand-up as a creative outlet, not even intentionally. I took what I thought was a comedy writing class. I had taken one in the past and it was all about scripts and sketches and sitcom pilot stuff. I thought that could be cool. You can meet some fun people and maybe we create some YouTube sketches or something like that.
I got to the class, I heard about it word of mouth. It was taught by a standup comedian I know. It was framed to me as comedy writing. It's a comedy writing class. I had no clue that it was actually a standup comedy class, even though it was being taught by a comedian. I got there and he said, after I paid him my money, he announced this to the entire group. “Everyone, welcome to my class. This is a standup comedy class.
Over the next ten weeks, you're going to learn how to craft five minutes of standup comedy. After the ten weeks, you were going to perform that five minutes for your friends and family.” My first reaction was I am not performing for my friends or my family. I'm not doing any of that. I'll just go through the class. I'll go through the process. Quite frankly, it was a pretty big class. There were about 40 people in there.
Not a lot of people were all that funny. There were a lot of senior citizens there and some much younger people. Here I am in my mid-30s, having watched a lot of, I wouldn't say stand-up comedy, but more comedy in my life. I liked going through the process and he would give us a little assignment every week and we'd have to get up in front of our peers and deliver it. I started to realize my stuff is so much better than most of these people's.
They were laughing and enough to the point where I said, after six weeks, I realized I'll do this final exam. I'm still not inviting my friends or family though. I don't need them showing up if this doesn't go well. I did it and I got laughs in front of a bunch of strangers at the “graduation show.” I was like, I want to do that again. I did do it again and I got even bigger laughs in front of a, let's just say a less friendly audience.
At no point did I think, “I have this figured out.” You just want to keep going as long as the feeling's good. The third time on stage or in the same venue was the second time. That was a disaster. I blanked, I bombed, I got heckled by a comedian on psychedelic drugs. The room was mainly comedians and it was very hard. I was up there probably ten minutes when I was supposed to only be up there for five, but it felt like a lifetime.
A lot of sane people would have never done it again. I said to myself, “I cannot let that be the last time I do this. Like that's the worst it's probably ever going to get.” It was when I said, “I want to keep going with this. It wasn't as bad as that third time. It wasn't as good as those first two times for quite a long period of time.” That's really where it started. That's how I got into all of this. I answered the question.
You answered a couple of questions, but where does it go today? Like, are you still doing open mics and stand up every once in a while? Did that continue for multiple years?
It continued for roughly twelve years. In my first six, I was actually on stage 3 to 5 times a week. I'd go to other cities. I'd go to Ottawa. I'm based in Montreal, so I'd go to Ottawa. I'd go to Toronto. I'd perform wherever I could, whenever I could. Now we're coming to the part of your question, I have been dabbling in a couple of comedy-related projects and the travel technology space. I won't get into all that.
In 2017, I thought to myself, “I could be a speaker. I wanted to speak on humor's impact on sales basically, and how anyone who speaks presents ourselves can use it as a weapon to earn attention, to build credibility and earn trust, to break the ice, to earn attention, all this good stuff, to be liked.” A lot of the things I still talk about to this day. What's one thing to be a keynote speaker of some kind? That's not really who I am. I'm not this speaker who comes on stage with a boisterous presence and is rehearsed for the day.
Everything's going to be perfect. This is what you do and all that.
I am not that guy. I'd like some comedians are a little flustered when they get on stage. That's always who I've been. Like you're trying to make sense of the audience, remember your material. That's who I am as a speaker. I said to myself, “This isn't even valuable enough, even if I was that polished speaker, it's nice, but I need something else.” When I was at Oracle, I had a pre-sales engineer who was dry, at least on the surface. He was actually funny when you got to know him. I was on a demo with him delivering the demo for a really boring financial consolidation product.
I teed off the demo for the vice president of finance and the controller. There's probably a manager of finance on the call and I tune out a little bit while he's doing the demo. At one point he makes some joke, some deep cut, insightful joke about the financial consolidation process and they laughed. I was like, “That was clever how he made that up off the top of his head.” Guess what? A month later, we're doing not to the same client, we're demoing the same stuff to a different prospect. He tells the same joke again and gets the same reaction.
At that point, I turned to my colleagues and said, “Have you ever done a financial consolidation demo with this guy?" They said, “Yeah.” I said, “Does he tell this one joke?” They're like, “He's been using that joke for years on prospect after prospect.” I realized at that moment that sales and stand-up have a lot of parallels. Even when I started doing stand-up, I was like coming at it from, everyone in the audience is, they're like a prospect or a customer. My job is to make them want to come back and either come back to this comedy club.
Follow me on social media because they find me funny. Like I have to get them to do something. I have to earn their trust really quickly by making them laugh fairly quickly upfront in short spurts before they go, “You know what? We're willing to give this guy some more of our time and attention.” I found there were all these parallels between go-to-market efforts, whether it's sales, whether it's marketing, and the process of being up on stage and being a stand of a comedian. That's how I started this business. Now I work with sales teams and we do two things. We go through a process of trying to craft a hyper-relevant piece of humor that shines a light on a problem that we as a vendor can solve for not even our ICP but for a specific target persona within the organization.
Comedy Writing: Sales and stand-up have a lot of parallels. Everyone in the audience is like a prospect or a customer. My job is to make them want to come back because they find me funny. I have to get them.
It could be level. It could be a low-level manager. They all have slightly different objectives and some are focused on tactical stuff and some are focused on big-picture strategic stuff. Our objective is to write some humor that can then be repurposed across 30 to 50 different touch points and channels. The list keeps growing of where you can use one good bit of humor. Even if they don't write a good joke, they do this all in breakout groups. It's meant to be a collaborative process. Even if they don't write a great joke, the big win is the process they go through because it forces them to think about who is my target persona and why should they care about us. What problems should we solve?
The Power Of Humor: Building Trust And Authentic Connections
Great. We do a lot of training on that. That's a great way of thinking about it. I love that idea of saying, “Let's understand them so well that we can craft this joke or something funny about the challenges or the issues or the environment.” The reason I was so excited to speak, Jon, I think there are so many things about this idea of just generally humor. Let's get away from the bravery of stand-up comedy, which by the way, I think you have to be shockingly brave.
All of us, by the way, have done well when we stood up at our brother's wedding and came up with a couple of jokes and had a great speech because everybody in that room wants us to do well. Very different when you're getting up and speaking in front of a group of people who paid money, they don't know you, and they're walking into a comedy club. They're actually not that keen on you doing well. Part of it was maybe like, they hope you do well, but you better do well because they paid to come in. It's a much more scrutinizing eye.
I don't think they don't want you to do well. I think they do because you're right, they paid and they're there for a good time. They're not there to, “I really hope that third one bombs.” We need to be reset because the first two made us laugh too hard. I think they do want to laugh at everybody. They want to laugh the whole night. You are right in that they did pay. If you relate to them and show them you understand who they are and what their challenges are and what their frustrations are on a day-to-day basis and be relatable to them, then they will not laugh.
With all these connections you're making, I see why you've got a business that aligns this with sales. Certainly, even with a workshop that we run, one of the things that's just so great about trying to inject some humor, not trying too hard, but finding that opportunity I find is it's so authentic. A laugh, somebody who's laughing and even near comes down fairly quickly. A lot of times in sales, you're trying to build some of that trust. You're trying to build some relationship. You're trying to get to an authentic conversation.
At times at the beginning, you come in from a place like Oracle or SAP or somebody of enterprise software, the buyer is rightly cautious. Maybe there's a little bit of a veneer or a wall. I think it's just such a human response to laugh that makes a very human connection. I think whether it's part of storytelling or whether it's just creating that connection, you cannot try too hard with it. I do think there's this great way of leveraging humor just to get everybody a little bit more relaxed.
Certainly in the early days in professional sales, when I was young, I would have said that because my personal life was so crazy in front of a young person living life, I thought I had to be so “professional” when I was at the office, there was this veneer. I probably came across as being uptight and very formal and I was trying to be perfect. Whereas I think in many cases, if anybody actually knew that I enjoyed a drink in those days, maybe stayed up a little bit too late, lived a rock and roll lifestyle. Probably would have liked me more because I was a bit more human, but I was always keeping that to me.
This idea of nowadays, by the way, I just am me everywhere. Whether it's we're running a workshop or something else, I'm just going to throw it in. I want to have a good time and humor has always been part of our family growing up, certainly part of my family now. All my friends are actually, I believe them to be very funny. A couple of them are extremely funny. This way of getting back together and laughing and using humor, just also, by the way, a good laugh, it just feels so therapeutic at times, just a good belly laugh, there's nothing better.
I agree. Yeah, absolutely.
Sales And Stand-Up Comedy: Resilience And Preparation For Success
By the way, but I do think back to yours standing up on stage, that idea of after you bomb, and by the way, listening to all these comedy podcasts I love, it seems like everybody bombs. By the way, anybody who's done anything material in sales, we've also bombed too. You've been in this business long enough, you've done this long enough. We've had big deals, we thought we should have won, they didn't win. Every once in a while it goes the other way. We've had great years, we've had some challenging years.
We've had fantastic bosses, we have terrible bosses. There's this resilience that I think that's required to make it through a career in professional B2B sales, managing those ups and downs. Part of it is you just keep going. Good things are going to happen, bad things are going to happen, but you just got to keep going and you kinda trust the process. It sounds like that's really what you did after show three before show four, two great ones and then one bomb, and then you go, “I got to get back up on this stage.”
I came up with this line when I started this business, which is whether you want to be an enterprise tech sales or you want to be in standup comedy, you don't need two business degrees like me. All these take our passion for failure. In the case of standup, that and a bus pass. You're right. Like, I really believe that resilience is important, but there's another step that both startups and salespeople really need to invest some time in.
That's preparation because like one of the topics I speak to sales teams about is what can salespeople learn from the worst open mic stand of comedians that I've had the misfortune of sharing the stage with in like twelve years of comedy because it was really interesting when I started. You're learning the local scene and some people are pros and like all you get to do is open mics even at the comedy, our local comedy club, the Comedy Nest.
You'd be on a mic on a Tuesday and there could be the biggest comedian in town. There could be some up-and-comers who are like, “I hope to get to their level.” They're not even big yet or any, or they're not even professionals, but they're funny. They're consistent. You see them on bills all around town. There were the people who are recent and starting and trying to make it. There was another group. There was a group of people who they do comedy maybe once a month.
They're doing it more than that, but they're never getting asked by a booker to be on a show where they get more than five minutes and maybe ten bucks. They're never getting a paid gig. They're never getting a proper spot, as we call it. They're just getting open mic spots. I watched them. Sometimes these are people who didn't understand how to relate to audiences. Sometimes, quite frankly, they were people a little bit later in life, were making dated pop culture references for a younger audience.
There was also the ones who they would get up there and like, it took them a long time to get to their first joke, to their first punchline. They would screw around with the audience a little bit. Whereas for me, I wanted to get my first joke off. My opening joke for years was that “I looked like Ross and Monica's dad from Friends.”
You do. Elliot Gould, by the way. There's a dated reference. Guys, Google Elliot Gould. Cool dude back in the ‘70s and ‘80s.
Let's talk about dated references and why you don't relate. I did start off by saying, “Yes, I'm Elliot Gould.” I forget the way I phrased it when I started. No one knew who Elliot Gould was, even in 2011, and 2012, when I started doing stand-up. I changed it to Ross and Monica's dad because that's how people in the audience knew who that guy was. Yes.
That took a little bit of failure and iteration, let's call it. I knew that I needed, when I come on stage, from the moment they called my name and I stepped up to the microphone, I have no more than 10 to 15 seconds to get a laugh out of the audience. That earns me another 10 or 15 seconds of their attention. To nail that joke, you need to prep a little bit. You need to like to have this mindset. I'm coming out there. I'm not screwing around. I'm not saying, how are you doing? I'm not like I'm not asking a question to the audience.
I'm just getting to that one thing I want to say to them that'll get that reaction I want that allows me to collect myself mentally so I can get to that next joke I've prepared. Just get to that next joke I've prepared. It's also going to be short. If I get a laugh, then great. I have a third usually. I always used to structure my sets. I always used to try and to my own detriment, to be quite frank, memorize everything and build a flow. I watched a lot of comedians who didn't build that flow. There is something to be said for trying to figure it out for yourself. I watched too many who didn't prepare.
Let's come back. This is a sales training class. Everything you're talking about is just a sales training class. First of all, just go to Elliot Gould versus Ross and Monica's dad. Speak in plain English to the buyer, whoever you're reaching out to. Forget the acronyms and the techno mumbo jumbo that they don't understand or makes them feel silly or they cannot connect with. Just speak in plain English, first of all. The second thing, I love this idea of go, “I walk up, I know what I'm going to do in the first 10 or 15 seconds and I'm trying to earn the right to keep their attention for the next 10 or 15 seconds.”
Prospecting 101. If somebody picks up the phone and I'm surprised, they pick up the phone. I don't really know what I'm going to say because it's so common that they don't pick up the phone. I got some mumbo jumbo and they go, “Who are you, what do you do?” I started spewing some irrelevant stuff like, “We've been in business 15 years. By the way, you were working for an Oracle implementation partner.” There are 10,000 Oracle implementation partners. How would you differentiate?
When somebody goes, “We already use Oracle or we use Offshore, or we use one of the other 9,000 companies.” You need a good answer for this. We need an articulate value proposition, not a joke, a value proposition, to earn the right to get somebody's time to have a little bit of an authentic conversation. The way you actually, obviously, your workshops are excellent and your speaking engagements are excellent. The way you speak to this is almost exactly how we would train SDRs or BDRs.
Like in thinking about it this way, I love this analogy with the standup. Thinking about, “I've got this process.” You said, “Listen, I used to memorize how I might go through my act or the other four or five minutes.” Now, you said there were some people who didn't do that. I think in sales, a real huge issue is too many people think I'm great. By the way, I don't need a process. I don't need a structure because I'm the world's greatest ad-libber. I should be on a stage doing improvisation. When someone sends them a curve, they just get kerfuffle.
They're drowning and they're going all over the place. They start creating objections and take it. Whereas if you do what you did, which is, “I've got a plan, but if it turns out when I get up there, you're killing the audience and they take you down a path, but you feel safe and you've got some connections.” You can go down another path. You still know where the guiding light here is. I still got my roadmap if I need to go back to it. That doesn't mean you cannot veer off it. That doesn't mean you're too structured and uptight. That's how we do sales training. That's exactly what we train on. This is awesome.
Improv Vs. Structure In Sales: Finding The Right Balance
It's fascinating that you mentioned the whole concept of improv. Improv, when I started this and I told people that my business is comedy writing for revenue teams, people would say, “That's amazing, I love improv.” I'm like, “No, I am the 180-degree opposite of improv.” I'm all about understanding subject matter so you can craft a message that gets repeatable, predictable reactions. Whereas improv is unscripted and it's about creating unrecreatable moments. People think there is this notion that improv is great for salespeople and it has certain benefits.
I will say, I think it's really powerful for listening. I think that's the biggest thing that you've brought you to do. My take is, if you become a subject matter expert in your prospects, the problems you solve for who and how they're impacting your buyers and understand how to quantify that and what questions to ask, you don't need to follow the script but you're also not going to be improvising. You're going to be having a conversation that's consultative that helps you determine if you could help them solve the problem and how much it's worth to them.
If you become the subject matter expert in your prospect and understand how to quantify that and what questions to ask, you don’t need to follow the script. You’re going to be having a conversation.
Even with that, Jon, at the end of it, I mean, you say we're not following a script, but you're definitely following a structure. I'm saying I'm going to be having this conversation. I want an authentic conversation. I'm in it. I'm actively listening, but I'm probably going to keep an eye on the time to a certain extent to understand, I'm going to get this to a certain level before I then figure out how am I closing for the next step with Jon, if and when I've made some connections between some of the issues and the challenges Jon has and some of the ways we've helped other clients in the past.
There is this idea that I've got this roadmap I'm going to try and get to. I know at the end, I've got to wrap this thing up at some point in time. The same way you understand when you're on stage that you don't have the stage for an hour. I've got four or five minutes, but I'm still trying to make that connection. I'm trying to get engagement, trying to get attention and interest. Maybe after the fact, they do follow me on Instagram or they do want to come to my next show and so on and so forth.
Bridging Comedy And Sales: Insights From Workshops
You start to think all of the things you've talked about here, creating a connection. We haven't even got to things like the resilience of handling objections with a little bit of humor, knowing your audience, storytelling, and breaking down complex ideas so people understand them. These are some fundamentals of a great sales conversation and authentic conversation about helping somebody achieve a business outcome. All of these things are just so applicable. I had no idea it was going to go down this path. Tell me a little bit more about what happens in some of your workshops or some of the other connections you've made between comedy and sales.
What happens in my workshops is we assign a team to write a joke and we give them preselected topic. It's usually to shine a light on the problem that the vendor can solve for the target persona or help them think about or consider some outcomes associated with not addressing the problem. That's where things can get very specific and humor is rooted in specifics, but it's also rooted in truth and pain.
Humor is rooted in specifics, but it's also rooted in truth and pain.
Outside of the business, we get business solutions rooted in pain, solving a problem. Tell me about comedy being rooted in pain.
What are comedians talking about? They're talking about things that frustrate them, I hate riding on air. Like the old one is airplane food. People are talking about online dating and how painful that is quite a bit. It's the things that drive us nuts, the things that keep us up at night. A lot of comedians say, talk about how the media fear mongers. That's a common thing on all sides of the political spectrum. There's only one comedian who I've ever seen, Ron Funches is his name.
Ron Funches, okay.
I'm not somebody who consumes all stand-up comedy. I watch some, especially when I was performing, you're around it all the time. You had a little less patience for some of the better stuff out there, especially Netflix specials. I watched Ron Funches, because I'd seen him at Just For Laughs, and he started off his special by going, that most comedians want to talk about things that they hate or make them angry or they're scared of.
I want to talk about things I love. At the same time, it really was still rooted, as I recall, in his frustrations with those things, and the pain around them. I had never even thought of that till that point, that like, we're only talking about stuff that drives us nuts and that people can relate to as a result because why are people coming to comedy shows? They're coming to forget about their day and laugh at the frustrations.
That's a huge one. I would say that going through the process, I challenge like my teams I work with to go beyond like, let's say I'm helping a company that sells sales technology. Sales technology solves this problem. Your technology solves problem X. “What is going to happen if they choose to ignore this problem?” “They're not going to hit quota.” I'm like, “Yes, but can we dial it back a little bit?” Like maybe it means that the right leads won't get to the right reps or CRM notes won't get entered properly or maybe it's sales and marketing are going to have a blockage with each other.
Like there are all these specifics of things that go wrong in every business function, and those are the outcomes we need to shine a light on and show how those particular specific costs of action are things preventing our buyer from achieving their real objective. We have to understand that in the first place.
Peel the onion back. At the end of the day, it's one thing to say, “We're going to miss quota.” Quite another thing to think about. Missing quotas is an interesting thing. Missing quota is going to mean, the company is not going to hit some objectives. Missing quota might mean we're not really helping clients the way we could be helping them so their businesses are going to suffer. If I'm missing a quota, people on my team are going to leave my team.
Depending upon the age, maturity level, the experience that could have a devastating impact on a new business professional. There are a lot of these downstream implications where the simple way of explaining this in 1998 would have been to say it was identify a need and develop a need. The truth of it is when we understand some of the issues and challenges, there are real implications to these things.
Sometimes somebody articulating or saying these things out loud causes them to really think about them for the first time and go, “We do actually have to fix this. We're going to make sure we hit our goals. We don't hit our goals as a company. It's not just my sales team that's going to get cut. There are other roles in the company where people are going to get cut.” I always think there's this tie into this bigger picture in the why.
Really the path there is turning that right to this authentic conversation with a buyer and I need trust and credibility for them to do that. I'm trying to figure out what's my path to do. It's not easy to build trust and credibility quickly with the new buyer. This is why something like humanizing the conversation as quickly as possible with something like humor is huge. Again, if it's authentic if it's a natural thing for you.
Understanding Your Buyer’s Job: A Key To Effective Sales
Look, one of the things I realized when I was selling Oracle applications and I'd be speaking with like a vice president of applications, some large company, it's like, I don't really know anything about this person's job. Like I know the basics, but I don't really know what they live through. At one point I said on some other podcasts, “Most sales pros sell stuff they've never used to people whose jobs they've never had and industries they've never worked.” That's why salespeople are looked at with a jaundiced eye by buyers because you're just a salesperson.
What do about what I do? Again, whether it's the humor, I use the word joke a lot. I don't mean a rabbi, a priest, and a minister. I just mean a short one-liner. The humor is connecting tissue between buyer and seller because it shows if a salesperson, whether they came up with it or not, to deliver a bit of deep-cut humor that shows you really understand the inner workings of their challenges. The negative impacts of them. If they can get them to laugh, they're also going to go, “That's powerful.” They're going to remember that. The memorability to humor, it's educational. It's like, our good friends at Challenger, like how can we show a commercial insight in a way that they hadn't considered and get the go?
If a salesperson can deliver a bit of deep-cut humor that shows they truly understand the inner workings of their customers' challenges, they're likely to be remembered. Humor is highly memorable.
I never thought of that or we do deal with that. Again, I think the process is even more valuable in the humor itself because if you like just go through the process of trying to craft short-form humor that follows certain rules, you're going to need to unearth a lot of knowledge, insight, understanding, and perspective about these problems and how they impact our buyers. It will inform you to be, again, more consultative and be able to zone in on. If I'm talking to a prospect, are they really a prospect?
Knowledge, insight, and understanding. By the way, we love Challenger with the teach, tailor, take, and control. When Matt Dixon has been on the show multiple times, what really great guy, very interesting. They wrote the book without a background in sales. They were researchers, met Matt and Brent and teach Taylor take control. It teach knowledge, insight, and understanding. We get the understanding when the buyer actually shares with us, but it's always this journey to get that connection.
Overcoming Fear And Nerves: Lessons From The Stage And Sales
They say a return on the time they're going to spend to share with us. By the way, speaking of time, we've got to be cautious of your time, but let me just go down a slightly different path, Jon, because again, I'm sure it doesn't seem like a big deal to you, but I'm pretty sure it's a big deal to anybody listening to this podcast. It's scary to get on a stage to do anything the first time. It's scary to be in sales. It's scary to pick up the phone the first time. It's scary to run your first demo the first time, although we don't love demos.
Scary to be in front of a senior executive the first time, where somehow they granted you the meeting. Now you're meeting a VP or an SVP of applications. It's scary. Even today, there's got to be those dates and times when you're going to step on a stage or you're going to do a keynote somewhere where the butterflies are floating around the night before or maybe the morning of. Tell us how you work through your process to actually get on the stage instead of heading for Kamloops.
Look, I think we got to practice. I think we got to know our stuff inside out to the point where even if we falter, it's not going to come off. Like we know when we falter. The biggest mistake I made in comedy was I mentioned earlier, I tried to memorize things word for word as I scripted them because I really bought into this whole notion of things like word economy, really being short and joke craft as we call it. Like how can you get to the punchline the fastest possible? Like ‘80s style comedy was predicated on that.
You were saying you would prepare too much maybe, so preparation helps you get on the stage because even when you go left to center, they cannot tell, you can tell, but they cannot tell. There's maybe you're cautioning over preparation.
What I was going to say was, as I'd be on stage and delivering, I'd like realize as I was saying it, “You inverted those words.” You deliver the punch line and you're just busy thinking about how you screwed up the setup and get in your own head. The audience didn't notice. They don't know. We're being hard on ourselves as it's going on, but it doesn't matter. People are appreciating it or getting it.
That's when you need to be connected to the room versus yourself. To connect with the room a little better, you just need to really have a good handle on your subject matter. You got to prep, you got to work on the timing. For example, I have a presentation coming up at a cybersecurity marketing conference. Guess what? I'm not a marketer. I'm not a cybersecurity guy. I don't really know. I'm an outsider, but I was asked to speak because I'm teaching messaging.
I had to come up with hyper-relevant messaging that marketers could benefit from in addition to salespeople. I'm really working on my deck right now. I'm working on the timing and the reveals of animation pacing. I think that's the work. Again, coming back to comedians who fail, I could tell some of them just were winging it. They'd get up there, they'd have a rough idea of three jokes they wanted to deliver. Some people really are okay with that, and for others, it just showed. You're not prepared and you're not working at this. Look, we all get butterflies, but preparation eliminates the risk of failure.
Preparation eliminates the risk of failure.
Preparation and putting in the work. Again, all of this stuff is the same. Any performance art is the same. Frankly, I think in many ways, sales is a performance art. We're still only spending a third of our time, a quarter of our time in front of clients or prospects. Professional athletes practice four times as much as they play. Who knows? Think of that workshop you did to get five minutes of standup. It's a month-long workshop, with multiple different sessions to write five minutes. Like my intro to my next story on the show takes seven minutes.
It's such a short period of time. The preparation, when preparation meets opportunity, amazing things happen. I do think the preparation shows nine times out of ten and far less worried about being over-prepared than under-prepared. I feel naked. My confidence comes out of the bottom of my feet if I'm under-prepared. If I'm over-prepared, I can work through it or I'll try and loosen up, but it doesn't work the other way.
No, one thing I wanted to add is that another lesson, it's just tied to some of the things that are floating around the ether of this conversation. When you have five minutes on stage, in 2024, you need to make them laugh, I would say twice a minute because comedy has evolved a little bit. In the ‘80s, it was, you need to laugh every 20 seconds. That's three times a minute which means you need to get to that punchline really quickly, which means the longer you ramble, especially when you come out on stage and they don't know who you are just like a cold call. If you keep talking, they're going to be, what's this all about?
I like to say that our goal is to make their faces light up, but not because they've just gotten bored and started staring at their phones. We got to graph type messages that people can digest simple language that elicit emotional reactions. That adheres not just for sales, but for sales development, for marketing. Everything I talk about is we're talking in the vein of salespeople. Every go-to-market function, they all need to be subject matter experts. They need to know how to trigger emotions, touch on that pain, and be short and quick, and punchy.
Using Humor To Address Pain Points In Sales Messaging
Well said, by the way. At the beginning, we were talking about you helping some of these companies craft a message that's leveraging humor to shine a light on a pain point or two. Do you have an example of that?
Yeah. I worked with a client, and I just want to add though, before I tell this joke that he's now the CEO. He told me, “I don't care that you wrote some jokes or that we wrote some jokes.” We closed some revenue off a cold email, which they did. He says, “The real value is the process and how it helped his new hires who hadn't even started on the job rant quickly because I was able to get them to express what problems they solved for who in simple English before they even started on the job.”
Nice.
They're a company, they're called TrustArc and they're a software who helps marketers and privacy officers manage their global privacy compliance efforts.
Very specific, extremely specific.
Very niche. In simple language, we all get asked to accept cookies, and cookie consent, and every website we go to, and every jurisdiction on the planet has different laws around that. A challenge that marketers and privacy officers have is they know this is a problem. They know they have to keep up with the laws or else they're going to get fined but they'll go to the CEO and ask for some budget. They're just like, “I don't know what this is.” The joke I wrote for them is, CEOs remind me of my parents. The only thing they understand less than technology is privacy.
That is good. I'm judging the comedy in any way, but that is good. Short, crisp, punchy.
Look, the reality is I'm not professing that we're going to write. Netflix comedy special-style jokes that are so cutting and so biting. The bar in B2B is pretty low. Everyone's really dry, everyone's boring. You just got to make it a little more human, a little more fun. It doesn't have to crush and destroy. Doesn't matter if someone drops dead laughing. You just want them to crack a smile and go, that's cute, that's clever. That's insightful, I like that. That's all we're looking for. We're just looking to get a bit of a reaction.
It doesn't matter if someone drops dead laughing. You just want them to crack a smile.
Comedy Heroes: Inspiration Behind The Humor In Sales
Who were some of your comedy heroes or when you were getting interested in this, and who do you like today?
When I was sixteen, which is not yesterday, I should have said which was just last week, there was a guy here in Montreal, his name was Sean Keane. Have you ever heard of this guy?
Rings a bell, by the way. For the readers, rarity, but I'm actually interviewing another Canadian on the show. Both Jon and I are Canadian. He does ring a bell, and you and I are probably not crazy different ages.
No, so Sean Keane. We were sixteen, we were underage, we were going to a comedy club that had just opened, and we hear like that MC calls his name and a theme song in like a ‘40s style theme song like the Andrews sisters start singing. I'm really dating myself but it was like that ‘40s style tune. This guy emerges from the back with slick back hair, sunglasses and like a trench coat and a suit and he's looking at us and staring at us and he's chewing his gum.
He just goes, “Somebody left their gum in the urinal.” He lets out, and we're sixteen. We're like, this is the funniest thing we've ever seen. He had a bunch of dark jokes. He wasn't like hyper offensive, but they were a little dark. We all just adored this guy, but he was the master of like short, quick, dark humor. He was an original idol. Over the years, like guys. I like Bill Burr. My tastes evolve. I like Sam Morril's a really good joke writer.
He's big. Mark Normand. I like Nate Bargatze. He's super clean. I don't care if they're clean or offensive. Like I just like funny. I don't really care. There was someone here, Deanne Smith. She's now in New York or I don't know where she is but she was a scream. Steve Patterson is always pretty funny. He's not like an idol of mine. There's a guy locally, David Pride, who's quite brilliant. I'm all over the board with it all.
I know some of those names. For me growing up, there was nothing better than Monty Python. The concept of the uptight Brits, my parents are British, so the uptight Brits, and then the look of absolute dismay when they get embarrassed or it looks like they're being silly, is just incredibly funny. Life of Brian is one of the funniest movies I've ever seen still to this day. You can keep watching it. In real formative years, when I stumbled on SCTV and it was just amazing to me that they'd be making these jokes and references, just like my brother and I would do that. I just thought it was the funniest thing ever.
It's too short-lived for sure. It wasn't long enough, but it was just truly amazingly funny stuff. It wasn't a funny situation. SNL always, to me, seems like a funny situation. SCTV were truly funny characters. You would continue to laugh. You just go anywhere with Ed Grimley or Guy Caballero. Of course, John Candy, there's Johnny LaRue. It's just so funny.
We didn't really get a lot of them in Montreal, but in my teenage years, I watched a lot of SNL with like Sandler, McMire, there's Dana Carvey. When you asked me the question, I was going with standups, but there's no doubt about it. SNL and some of these like the naked gun dumb and dumber movies, are the real combat.
Dynamite. Animal House. Go back and watch. A lot of the folks reading to this may not have heard of a movie called Animal House. It's still funny. It's a bit dated, but it's just ridiculously funny.
I watched it recently for the first time. I will disagree.
You watched it. First of all, you look like Ivan Reitman. The director, if you look at him back in the day, he also looks a lot like you. Just love the movie. We'll resolve that another time, Jon. First of all, thank you, for joining us on the show.
Thanks for having me. This is a lot of fun.
It's a lot of fun. The people reading are going to want to hear more. This connection between comedy and how you use it to train the sales team. How do they find out more about you or connect with you?
Look, there are two real ways to get ahold of me. Number one is LinkedIn. Drop me a line. Let's connect. Jon, there’s no H, Selig. That's also my URL JonSelig.com. My business is comedy writing for revenue teams. Just draw me a line through my websites. You can even somehow get ahold of my email there, but LinkedIn's a great place to connect, and let's have a conversation there.
Folks, as we think about trying to do something unique for our sales organization, something like Jon's approach, I think it's fantastic. We've got clients, we're going to be thinking about this for two. Jon, thank you again for joining. What a great conversation. Team, thank you for joining the show.
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We run this show because we have this mission of increasing the professionalism of B2B sales because we know if we do that, we'll actually improve the lives of professional salespeople. We hope you enjoyed the show. If you did, please like and subscribe to the Selling Well podcast because that's actually how we get great guests like Jon when you do that. Now, the other thing is, team, we're growth-oriented.
A lot of the things we do in the podcast are because you gave us great suggestions. Please keep them coming. You can send your suggestions to us at MarkCox@InTheFunnel.com. That's my personal email. I personally respond to every suggestion we get. We love constructive criticism. Keep it coming our way. In the meantime team, we'll see you next time on the show, and tell your friends about this podcast. Thanks for joining us.
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About Jon Selig
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).
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. As he says, his 12 years in sales was a well-paid internship for his career in stand-up comedy.
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.