How to Make Outbound Work and Build Pipeline in 2026 (with Jen Allen-Knuth, Founder of DemandJen)

Hey, it's me, Dave. Our friends over at Customer I.O. are sponsors of today's episode. They're a really cool company that helps marketers turn first-party data into engaging customer experiences across email, SMS, and push, and they built their platform for marketers who actually care about the craft because marketing is a craft that takes creativity, thought, and taste. Right now, everyone thinks they're magically a marketer because they have access to AI, and the result is kind of painful. More robotic emails, more noise, more bleh. AI isn't magic. It's not going to fix bad strategy or write great copy for you magically, but the best teams also aren't ignoring it. They treat AI as infrastructure. When it's built the right way, it actually makes marketing feel more human, not less. And that's what Customer I.O. is doing. Their AI handles repetitive work like setup, orchestration, and tasks that should be automated so that you can focus on what actually matters, the craft of marketing, the strategy, the creativity. This is how good marketers are using AI right now, not to replace thinking but to support it. If this landed with you at all, this idea about the craft of marketing, I want you to go and check out Customer I.O. It's customer.io slash exit five. Go and check them out customer.io slash exit five. Hey, it's me, Dave. Today's episode is brought to you by Consensus, the interactive demo platform. Look, most of your buyers have already decided whether they like you before your sales team ever gets on a call with them. They've asked ChatGBT and Clawed about your product. They found reviews about you online. They've talked to peers who've used your product before. And by the time they hit request a demo on your site, they've often already come to a decision. So you're losing control of the narrative before the first touch point. And now they have to wait three to five days for a demo. Consensus gives you that control back. They help you meet your buyer where they actually are with interactive, personalized AI demos that live on your site. When a buyer shows up wanting to poke around on their own terms, you give them what they want. Plus, you get to see exactly who's watching, what they clicked on, and who the decision makers are. So stop being a bystander while LLM sell or even unsell your product. Category leaders like Atlassian and Autodesk use Consensus to turn invisible researchers into high-intent leads. Go and check them out at goconsensus.com slash exit five, goconsensus.com slash exit five. Hey, it's Dave Quicknote. Before we get into this episode, this is a recording from Drive 2025, our annual event here at Exit Five. This was recorded live in Burlington, Vermont at Hula as part of our event. And we'd love to have you at next year's event. We're bringing it back to Vermont, Stowe, Vermont. You can go to exit5.com slash drive to get more information. Put your name on the waitlist and maybe make it to next year's event. But we're bringing the audio recordings from these sessions to you live, well, recorded on the podcast because we thought it'd be a fun way to show you the stuff we talk about at Drive and give you a sense of what it was like if you didn't get to be there. And if you were there, then you get to now re-listen and maybe take notes again. So this is one of the sessions from Drive. Go and check it out. Get tickets, put your name on the waitlist for next year, exit5.com slash drive. Our next speaker, this is Dave. This is somebody I've gotten to know through the joy of LinkedIn over the last couple of years. Since this is a room, how many people work in marketing in this room just real quick? All right. Shit. You might have to see yourself out, ma'am. So since we all work with salespeople in our day-to-day, I thought it would be, you know, useful to hear from someone in that world. So we asked Jen to come to Drive. After 18 years as a frontline seller at corporate executive board in the Challenger sales, she saw firsthand that one of the biggest threats to close one deals wasn't the competition, it was buyer status quo. Or the annoying ass CEO can't get out of his own way. She went on to become the chief evangelist of Challenger and head of community growth for Lavender. Now she's the founder of DemandGen, where she trains sales teams on how to unstick stalled deals, create status quo, busting outbound messages, align the buying team for change, and avoid the tragic fate of losing to no decisions. She's here to talk about building pipeline in the shiny object era she rocks. Please give it up for Jen Allen Canuth. I have always wanted to walk on stage to be Jane Brown. So here we are, dreams coming true. First of all, it is wonderful to be here. Before we talk about any of this stuff, I want to take a moment to acknowledge someone and something. So I, for many of you that know me, am a massive rescue dog vet. Like if you know me, if you follow me, if we're connected on LinkedIn, I post every Saturday about a different rescue dog. It's a huge passion of mine that many of you don't know where it started. It started 13 years ago when I adopted my first dog, Mugsy. Okay, now Mugsy, I got from a shelter. When I was 30, I don't know what y'all were doing when you were 30, I was an animal. Like I probably would have benefited from being locked up in a shelter kennel for my own good. And Mugsy, my very first dog, gave me a totally new sense of purpose, and he gave me a cause to be passionate about and something I care about. So why am I telling you this? Well, many of you maybe have noticed that I just showed up today. I was supposed to be here on Tuesday. I was supposed to stay til Friday. I was so pumped because there's so many people in this room that I'm so excited to meet and see in real life. And on Monday, I got some pretty devastating news. And basically walked into that appointment and walked out hearing that my dog has an inoperable tumor on his jaw. And there's really nothing we can do about it, which is a shitty place to be, frankly, when you feel helpless. And so frantically, I emailed Dave. And I'm like, Dave, I know you're probably boxing up a bunch of shit to come here and doing all the things, but is it okay if I get there really late Wednesday? I miss a bunch of stuff. And then do my talk on Thursday, shorten it to 45 minutes, not an hour, and then run out of here. Now Dave and I have never met in person. And I am like a total warrior. So I'm thinking he's going to be like, of course you're flaking. You're a salesperson. I knew I shouldn't have invited you to this thing. I knew it. But Dave responded with one of the kindest responses ever. He said, of course, no problem. So glad that you're making time to be there for what's important. The shit. And so I said, I used that super, I used superhuman AI, that email AI tool. He's like, I replied. I hit that one button. And so I just think like we're in the middle of a crazy week right now. It feels weird to stand up here and not acknowledge it. I think like we all have our handfuls of shit, whether it's personal shit, whether it's shit at the job, whether it's like me, you've got four dogs, and it's actual feces that you're picking up all of the time, all of the time. And we all have our shit. And I think it's just so important that we have moments like this and events like this and communities like this, because this is what I think actually matters, the stuff that matters. So I just want to shout out Dave for being an incredible human being. Making him blush. So with that, talked a lot about shit in the first two minutes here. So let's keep that theme going. Speaking of dealing with shit, raise your hand if you deal with your sales team inside of your business. Okay, lots of you. Wonderful. Dave, as he mentioned, thought it would be a fun idea to bring a different perspective up. So I've been a lifelong seller. I work with sales teams all the time now, companies big and small. And I think it's always been the case that a lot of times we're at odds with each other, right? Sales versus marketing, we're finger pointing at each other. What I hope to do in the 40 minutes that I've got for you today is to give us a common enemy to rally around. And that is the enemy of buyer status quo. I'm big on tactical stuff, so I'm going to spend a few minutes talking about the problem of building pipeline and what I lovingly refer to as the shiny object era, which is the era we're living in where literally every second there's a new game changing revolutionary technology that upends the way that work gets done. What that means and how that's playing out differently on the sales side, because I don't think this is something we can win in sales alone or in marketing alone. I do believe it's where we're best served by being aligned. So I'm going to give you a couple ideas. I'm going to give you two zero dollar exercises. They are my favorite kind of exercise. They don't cost you anything that I hope you take back to your business to really get after this problem. Now, before we do that, we have to dispel a myth, okay? And I need your help to do it. I want you to think of any TV show, movie you have ever seen that portrays a salesperson and tell me who comes to mind. My girl, Dwight Schrute, Tommy Boy, what else? Glenn Gary Gunn Ross, you, Michael Scott, who else? Ben Affleck, I haven't heard that. What's he? Oh, duh, sorry. I should totally have seen that movie as a salesperson. Okay. So if you think about all of those people with the exception of maybe Dwight and Tommy, many of those people are the people that come to mind for me, right? They are closers. So you've got Don Draper, who's actually more of a marketing guy, but I would put him in the sales bucket. You've got like Jordan Belfer, does anyone say him? The Wolf of Wall Street. And you got Glenn Gary, Glenn Ross, right? You got all these people. And this portrayal of salespeople is largely why I never wanted to go into sales, because I didn't see myself in this. Because the way they portray it in TV and movies is like, all you have to do to be good at sales is just be a middle-aged white dude put on a really fancy suit, walk into a room, say the magic words, and close the deal. It's all about charisma. Now, when we think about reality in the 21 years I've spent selling, it is rarely these people that are winning in sales, right? Because you can spot them a mile away, and we personally don't really enjoy spending time with these folks, right? I mean, some of you may, and there's weirdos in every room, but most of us don't enjoy that. What I find interesting is if you look at the data, so there was a study that LinkedIn did a couple years ago, and it talks about what are the most valuable qualities that you value in a salesperson, look where charisma is on the bottom. I made it really easy. I put a big old red arrow there. It's at the absolute bottom of the list. And when you look at what's at the top, it's trustworthiness, it's transparency, problem-solving ability, understanding of the industry. In my opinion, that stuff has very little to do with closing. That's the stuff that has to do with opening a deal. Yet if we look at how we've treated pipeline generation, demand generation, whatever we want to call it, often we give it to the least experienced people in the business, our loving SDRs. Or now we're like, hell, let's nobody touch it. Like, let's let AI do it, because none of us want to be involved in this thing, right? We treat it as an afterthought. When in reality, I think anytime we meet someone, so I'm sure there are people here you wanted to meet, you would never make your introduction to that person an afterthought. But in sales and marketing, often we do. And so this is a room of marketers. I'm talking about building pipeline, but specifically building pipeline in the shiny object era. To explain what I mean by that, I am going to use you as my loving example. Now, and we've got lots of different roles in the room, but many of you are probably familiar with Scott Brinker's marketing landscape map, right? We all know it. Okay. Now, when Scott Brinker started doing this, it was back in 2011, there were 150 different marketing technologies on one page, which is like goes against every PowerPoint presentation design principle in like that ever existed, right? There's 150 logos, it was messy, it was loud. Fast forward to May of this year, it is 15,384 logos on this page. Now you can see they're boxed into each one of those boxes. And I think in sales and sometimes even in marketing, we tend to think about our direct competitors a lot. So who else is in my box? That is a terrible thing to say in front of a public room. Who else is in my box? And we have to defeat them and show how we're better than them. But in reality, what makes this so hard, and y'all live this, so I know I'm preaching the choir, is all of these people are trying to get a bit of your time, your attention, and your money, right? So even though they might think, well, these are only our competitors, it's really everybody on this page. And as more and more companies pop up, well, there ain't a lot of companies out there being like, you know, we're probably like a strong three, but you should really consider us because we've got a great team. Everybody's claiming to be the leading provider of this and the number one of that. And on the other end of it are y'all, right? Probably sitting there with headphones on, being like, shut up and leave me alone. It's why so many people say, cold outbound is dead and all these things are dead. I strongly disagree with it. But on top of it, I know we have been taught to have a giant erection for AI. However, AI is just making this worse because we've always had the stuff on the left. Like let's talk CRMs. Like there's always been the sales force in the HubSpot. And then as you move down, you've got these like Challenger software. And then you get some like verticalized software. Like I just did a session with Intap and they just focus CRM on professional services. And then you get like services software. And then you start to see the startups pop up early stage, late stage. But now there's this crazy long tail. And it's not new, right? We've always had the opportunity to build software in-house, but it was too expensive. It required too much talent. And so it was just often easier to say like, we'll just buy it from someone else. But now low code, no code, whatever code we want to put in front of it. Now there's this entire different category saying, well, forget that, just build it yourself. And we as humans, we like to like fiddle and tinker and do all these things. And so for sales person's perspective, even if we take the last page, not only am I competing for time, attention and money against 15,000 other companies, now I got this on top of it. This is what I refer to as the shiny object era, because if we are all screaming about how we have the best solution, we, everybody tunes out, right? It's like going to a concert, I was just having a conversation with someone about concerts. It's like going to a concert and you got three acts performing at different ends. And like this act wants more people, so they turn their music up louder. This act wants more people, so then they turn their music. And then all by the end of it, you're like, just get me out of here. Which I think is honestly the state of pipeline generation today. When we look at our natural response to this, when we think about pipe gen, I'm literally going to lose my mind if I hear one more person say, well, let's just make more dials. Let's make more dials, that'll solve it. Or let's send more emails, or let's do social, or let's do things, as if there's something that we do that no one else has figured out. There's a finite amount of channels here, right? And just doubling down on more worked before, like no dig against it. It's not as effective now. Would you agree? Like screaming into the void is not a terribly effective way. So if you look at the data, what the data tells us is if you just look at the opportunities that are in your pipeline now, and your sales team's pipeline, what's in there right now, 38% of the opportunities that are in that pipeline right now will simply be lost to the buyer saying, hey, I might even agree that you have a better way, but we're fine with good enough. That is a frustrating way to lose. When I was a salesperson, my number was probably more like 65, 70%. I would have killed for 38%. But I was selling a sales methodology, and ain't nobody in the world needs a sales methodology to keep their lights on. The problem for your sellers and the place where oftentimes sales teams don't fully understand it is no buyer in the world has ever hung up from a demo or a sales call and said, thank you so much for the time, Jen. I have elected to choose status quo. I think that's a weird thing to say, even though we do it all the time. Instead, they'll say things like, let's revisit this in six months. Now, when I was a salesperson, I was like, game on. I'm putting that six-month mark reminder. I'm calling you on the freaking day because I'm diligent and I'm hardworking, and I want your business. And I'd call up and I'd say, hey, it's Jen. Not sure if you remember, we met six months ago. You said now would be a better time. Meanwhile, that buyer, 10 times out of 10, was probably thinking, I thought you'd be gone. I thought I'd be gone. I thought we could just avoid this entire situation. Because anytime we tell a salesperson, no, what do they do? They're trained to objection handle. Who likes to be handled? Sometimes I like to be handled, not by a salesperson. Not by a salesperson. And so this is punting off into some distant future, hoping this problem goes away. Second one, we don't have the budget. I loved hearing this because I'm like, well, that's not a me problem. That's a buyer problem, cheap. What this was actually was I have budget because when businesses have problems that are important and urgent, we find ways to get it done. This was just the buyer nicely saying to me, I just don't have a budget for this because I actually don't think I need to do this right now. I got to do this other stuff. I'll socialize and get back to you, kiss a death. I moved that puppy right forward in my forecast. I'm like, they are talking about it. No, they weren't. They were hanging up for me. They were going into five more calls. And at the end of the day, they're like, do I really want to be the idiot that is going to say, let me build a business case. Let me get 20 people to agree to doing this. Let me talk about change. No, it's just much easier to let it lie. The closest to the truth is probably we're good for now. And this is where it's so frustrating to watch this happen again because I watched it on my own deals all the time. Now sellers do what we're taught to do, which is objection handle. Now I'm going to play out. Remember the sell me this pen scene from Wolf of Wall Street? So I'm going to play out sell me this pen in modern sass times. So Leo, we offer a revolutionary solution for scalable handwriting workflows. Meanwhile, your buyer is like, I don't know what you're talking about. I think you might be talking about. All right, I already have a pen. I'm good status quo. Now objection handling. But we were ranked a leader on Gartner's Magic Quadrant. We deliver a 10 times ROI. Do you want to see a case study about my pen? No, I don't. Right. And if you watch Jordan Belfort, which I don't try to do a lot, but I did do one time, what he talks about, he's like, my goal with sell me this pen is just to figure out, do you need a pen or not? And that's fine if you're selling something that someone wakes up in the morning and says, shit, we ran out. When do we get more? But I don't know a lot of people who wake up and they're like, oh my gosh, we're out of intelligent workflow solutions and where do I get more? We are selling things that are categorically disruptive and are different than what people have normalized in terms of like, I need this because we're out. And so this type of logic, this type of sales conversation, this type of like, let status quo appear and then we objection handle it really falls apart. And it's why status quo wins more than we do. If you haven't picked up on now, I love Chris Farley. Okay. Now, when we let status quo come up in a deal, when we lead with our product and we lead with how awesome it is and we talk their ear off and we demo and we rush into all that stuff, what we often fail to do, what I fail to do a lot as a salesperson is ever help the prospect decide, do I even have a problem worth solving and worth solving right now? Because I can sit here and watch your cool tools and watch your cool technology and watch your AI do its AI thing. And I can hang up and make you think that I loved it and then realize like, as cool as it is, we've got a way to solve the problem and good is good enough. And so we're going to take you is two sections. If we want to stop losing so much to status quo, it requires we do two things. One, requires as a business, we understand how big the status quo problem is for us right now. I'm going to back you into a way to figure that out. And the number two, it requires that we help our customers, our prospects understand how big their status quo is to them. Do the mental math on that. So the first part is about like kind of getting alignment with the sales organization. The second part is getting alignment with your customers. Now, y'all have CRMs, right? I just thought it'd be a stupid question to ask. Yes, of course we do. All right, you have CRMs. When a seller loses a deal and they have to move it to close lost, what are some of the close lost reason codes that you all use? Just shout it out. Budget, timing, competitor, implementation. What? Went cold. Went cold. What else? Empty. Like empties and our souls. We're just, I'm empty. I got nothing left. I got nothing left. Okay. So tell me of all of those reason codes that we just looked at, which one is the salesperson saying, yo, I just didn't actually do that good of a job? Maybe, never is really the answer. And that is because every seller who has ever carried a quota in history is the co-author of this book. It's not my fault. It is somebody else's fault. The problem here is we're asking salespeople to grade their own homework, and we are never going to throw ourselves under the bus. It's always, they don't have the budget, not, they have budget. They just didn't, I didn't make a compelling enough argument that we should have some of it. It is lack of ROI. And the more concerning issue that I empathize for the people in this room is often then the finger goes not to the sales rep, but to y'all, which is like, we need to rethink our pricing model and we need more case studies and we need more ROI and more, more, more, more, more feed the beast. Right? Like as if one case study from some random ball bearing manufacturer in Shevoygan, Wisconsin is going to solve the company's problems. And so you all end up getting blamed, even though in most cases when I'm working with sales teams, it's what's happening inside of the sales cycle. And the unfortunate thing is it's totally preventable, right? We lose deals we could otherwise win. It's not that our product's not good enough. It's not that we don't have a good enough brand or fair enough price. We're just losing against status quo. And so if you look at it, the thing I wish I learned about sales way sooner, is sales is actually not that hard if you just understand basic human psychology. Like humans are the most predictable creatures in the world. And so what happens is anytime we're met with uncertainty, risk, any of that, we default to thinking about these two brains. So on the left, you've got your rational brain. So if I'm looking at a tool, maybe I inbounded it, let alone outbound. And I'm listening to you and I'm like, man, this is like a lot more than I signed up for. And I have to make a business case and I have to get other people on board. And I'm already so swamped. And do I really want to put my neck out on the emotional side of the brain? It's the what if monster. What if I do go through all that? I do all that work. I change how something is done today. And then people look around after and they're like, why'd you change it? I liked the old way. That's political capital. Now I'm risking. So these two things come together. And like this is the most basic, simple statement ever. But I don't think I really appreciate it as a sales person is that we are often creating messaging around the idea of we are better. But I lost more than anything else to your right. You do have a better way. We got like Bob in the back doing sales training and he sucks at it. But Bob is good enough and we're okay with good enough. All of a sudden, all this stuff we've been taught in sales breaks down. It is almost impossible to objection handle good enough. Hey, it's me, Dave. This episode is brought to you by our friends at NAC. NAC is a no code email and landing page creation platform focused on a problem every marketing team runs into. Have you ever had a really good marketing idea, but then it takes forever to actually ship it out the door? It's usually not because your idea is bad, but because the process in the middle is slow. 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And when we try, it sounds like this. What if I give you a 15% discount? Like what is about 15? We just always think like 15 will do it. It's the way to do it, right? So what if I just make this thing that you don't think you need a little bit cheaper? No? It's still too expensive? Okay, I'm going to note that as a salesperson. Well, what if I show you all these ROI studies? Look at all this value everybody else got. Don't you want to be like them? As if we are not all picking our best customers and putting that in the ROI. Like we're never being like, this was like a mid-tier rollout, but they were, they enjoyed it. This is how we respond. And then when we get a no, we come back to you and we say, well, it's because we're too expensive. And it's because we don't have enough ROI stories. Please just show of hands. It's just on my own weird curiosity. Like how many times have you heard we knew more ROI case studies, more stories? I'm sorry, on behalf of the people that I work with. Okay, so first zero dollar exercise. A close loss audit. Now as a salesperson, I used to do this on my own territory. It is much better when you do it across the board. But if you have a tricky relationship with your sales team, maybe go to your best salesperson, start there, get them to be your groundswell. It's very simple. All you're going to do is you're going to take any deal that has been closed lost between January and September 11th. And you're going to include the pipeline value that was forecasted for that. So you got the deal pipeline value. And you're going to filter it by anything that sounds a little bit like status quo. So unresponsive, budget, no champion, value, which is the weirdest closed loss reason ever. Like of course value always in play. You're going to take those and you're going to filter that list for anything that kind of sounds like status quo. It's not an exact science, but that will give you a rough estimate of how much we are currently losing to status quo today. And the reason that matters. So back in January, I was working with a really large company, Martek Space, everyone would know, and they had never looked at their closed loss data that way. So I said, why don't you go back, look at 2024 data through that lens. And they came back and they said, we found $53 million of closed loss opportunities due to status quo. And the most frustrating thing about that is the marketing team was absolutely being hammered of we need more pipeline, we need more pipeline, we need more pipeline. Meanwhile, you got all this pipeline over here. We probably could do something with it. But the reason I did this with another legal tech company, they came back with much smaller, they came back with $15 million. It's not to say we make those that go away. But if you make a 10% dent in a $50 million problem, I'm no mathematician, but I think that's like $5 million. That is a sizable opportunity. And so the way that I've done this with organizations, but you don't need me for it, is to say, listen, I've been thinking a lot about our pipeline generation problem. I've been thinking about the opportunities we brought in. And I did some analysis to look at where I think we might be losing the status quo. And I'd like to just kind of go over it with you. We don't have to talk at them. I think a lot of our problems in sales and marketing alignment is talking at. But let's look at this together. Because what happens, and what I've seen happen time and time again, is it gives us a common enemy to fight against. And I don't think anybody wants the answer to be like, let's just go build more new pipeline. We got this much sitting on the shelf today. So this is an exercise that can spark a really productive conversation with the sales team. Because the sales team doesn't want the answer to be build more pipeline either. I can tell you that right now. And so if we can come together and say, let's size it, see how much status quo might be hurting us, that gives us the opportunity to think differently about our messaging and how we go to market, which is part two. So you can't solve, like there's no point in solving a problem. You don't even do this section. If you can't get alignment with the sales team, that this is costing us first. Like that's why that part comes first is because you need alignment there. Once you get alignment, now it causes us to probably think a lot differently about our messaging. Now, I am not sure if you are aware of a very serious epidemic that is affecting everyone in sales marketing product. It is an epidemic that I refer to as the wee wee problem. Now the wee wee problem, I am a one person sales trainer. I am not like any of you in this room. You're way more important. You're way more like your titles are sexier. This is my inbox. And the most common words you see in this preview text is I, we, our, our company name. Which means when we go to build pipeline, we are just wee weeing all over our prospects, all over them. Okay, we're talking about wee wee. We're talking about dog feces. This is my talent. We are wee weeing everywhere because that's what we've been led to believe that we need to do. Show how we have a better way and why we are so much better. Meanwhile, our competitor that we're trying to fight against is status quo. Status quo doesn't care if you're better. You can win the argument that you're better and still lose the deal. And so this means, in my opinion, we have to think differently about our messaging strategy when status quo is a competitor. So what I'm going to do is I'm going to give us a fictional scenario where you all work for me now. This is the power trip that I have being on a stage. And I'm going to walk you through how you go from a very wee wee focus message to a message where you don't talk about your company, your solution, your product at all. And then I'm going to organize it around the four questions that I don't care who you sell to, how you sell, what you sell. Everybody in this room can take back an answer on behalf of your organization. I would highly encourage you to answer it with sales, with product, with executive leadership because if you all do this in your little tight, cozy rooms and then come back and say it, we're all going to organ reject it. So this is meant to be an exercise that we do together. So you work for me now. You work for Jen's Packable Raincoat Company. Now, Jen's Packable Raincoat Company is a product where we have a raincoat like this big, fits in your bag, never have to remember to pack it. It's always there. Keeps you drier unlike an umbrella. Your umbrella inverts in the rain. That never happens. So in this scenario, we have a better way to stay dry. Now, side note, nobody in this room, I don't think, is selling raincoats and competing against umbrellas. But you are because raise your hand if you own an umbrella. I'm just looking for the weird. You don't own an umbrella. You're like, you just like stone-colded me too. You're like, no, I don't. Yeah, sorry. Okay. Most of us own an umbrella. Most of us have a way to solve the problem, just like your prospects. Like people get this idea of, we're going to talk about cost of an action a bit. People get this idea of cost of an action, somehow means like cost of doing nothing. That's offensive. If someone has a known problem, they're not doing nothing about it. There's something they're doing. And so for many of us, the problem is staying dry. We have an umbrella for that, just like your prospects. If their problem is generating pipeline, they've got some taped together method for doing that. So what do you think happens when you pitch your very sexy, better way to stay dry raincoat that costs $100? What are most people going to say? I have an umbrella. And what else? Yeah, so cheap. This is expensive. Right? This is too expensive. If I was a salesperson selling this raincoat, I would be like, closed-lossing all my deals. Like, oh, too expensive budget pricing. It's not me. It's them. So what we tend to do, and I can say this confidently, because where I spent a lot of my time, Brendan loves this line, I am a pervert for cold email. I read cold emails from sellers all of the time. And I will tell you, maybe not as extreme, but most emails I read don't look that far off from this. So I just asked ChatGPT to generate an email to sell this packable raincoat. I'm not going to read the whole thing, but I will tell you some highlights. Don't let inclement weather disrupt your outerwear workflow, rocket ship, because we always need a rocket ship. Hope this message finds you well. A Gents Packable Rain Company were revolutionizing the precipitation preparedness landscape with our next-gen AI-adjacent packable rain care solution built for scale optimized for agility. We understand your problems with surprise downpours and jacket and efficient thieves. These are all our features, and we would just love to hop on a demo to talk through the raincoat and share our recent white paper disrupting drizzle how our wear is eating umbrellas. Stay dry, Zach, the drizzle disruptor. Enterprise Rainwear Evangelist, the future of dryness is now. Okay, not every cold email is this bad, but I swear to you, y'all, there are sellers on your teams right now that are sending trees and shit like this, because if I don't have to write it and someone else will, I can be like, well, this thought it was a good idea. So the choreography of this email is what we need to stop, right? The choreography is, hi, I'm Jen. I'd love to talk about myself for the next, like, 500 words, and here's all our features, and this is why it's better than the alternative, and I would just love to get your time on a demo. How many times do you get outbound that sounds like that, right? I feel for this group, right, because I feel like you're at the brunt of it. As we talked about before, you might have the best damn raincoat in the world. If it's $100, it's too expensive, right? And so this is this in play, like, better raincoat, better way to stay dry does not mean I abandon my umbrella, because quite frankly, my umbrella is free because I already own it. That's a tough thing to overcome. So the missing ingredient, the thing that, when I read out Bonnie Mouse, I am craving, is something called perceptual curiosity. Perceptual curiosity is defined here. It is a very specific type of curiosity, which is like when you hear something that contradicts what you think you know or believe to be true, and they describe it as like an itch you need to scratch, right, because you're now on this mission to seek out information. So I told this story recently, but there is a study that was done of public bathroom stalls. This is disgusting, and I'm clearly toilet humor is my shtick. There is a study of public bathroom stalls that shows most of us, when we go to a public bathroom, we go to the middle stalls, no reason why it's subconscious. But they're actually the dirtiest stalls. It's the end stalls you want to use because so many of us go to the middle stalls. Now, when I heard that, I freaking told everybody I knew. I was like, guess what? You filthy animal, because we as humans love to feel smart. We love to feel funny. Like we love to be perceived that way. And that, I would argue, is what exactly we want out of a message. We want someone to start thinking about what they think to be true, what they believe to be true, and start seeking out, why is this different from what I know? Because that sparks this snatch. If you can get someone to say, wow, that's different than what I believed, they now want to go and tell everybody, which is, I promise you, everything your sales team wants that prospect to do. And so I'm going to show you the four questions to get to this. And I think this is an ingredient, when I see this in a cold email, it's very rare, but it looks and sounds different from every other cold email I read. So question number one seems crazy obvious, but I can tell you most sales teams don't do this. Who is most likely to have the problem that our solution solves? When I was a seller, I was like, let me prioritize my territory by sexiest logos, most FTE, biggest revenue size, right? And let me find a way in because if I can win that deal, man, I will be the boss. I chased deals for years that had no business chasing because they didn't have the problem that we solved. So in this example, if I'm selling this raincoat, I'm not going to focus my time on Phoenix, no shade to the Phoenix people in the room. Thank you. But I'm going to focus on the cities that have the highest precipitation rates. Now I'm from Chicago areas, I'm going to pick Chicago for this example, 119 days of rain a year. So who in your prospect universe is most likely to have the problem that you solved? Question two, now how do those people solve the problem today? And more importantly, why? So for an average human being, most of us own about two umbrellas. It doesn't matter if you own three or 20, that's weird, but like more power to you. But the reason we own them is because they're so cheap, right? It's like an umbrella costs, I don't know, I haven't bought an umbrella a long time. An umbrella doesn't cost that much. So yeah, I'll pick one up and I'll keep it in my car. So we have to be able to empathize with what makes status quo attractive. This is not where we're judging. We're not saying, well, you just don't know there's a better way. I don't think that's true. We like status quo for a reason. We've got to understand that because question three is now, what is the unintended negative consequence as a result of how we're solving the problem today? So as it turns out, only 5% of us remember to pack an umbrella on days it's supposed to rain. I am 100% part of the 95% that forgets. Is anybody else? Yeah, is anybody part of the 5% like you just like got your umbrella right here? Yeah, okay, I like it. There's always a couple of 5%. All right, so I'm Dutch. I'm Dutch. Yeah, it's fair. That is a fair reason. Now, when we forget most of us, not all of us will do what? We order an Uber or a Lyft. Like if you're in the lobby of your office building and you've got a huge client meeting and you were planning to walk and it's like 0.6 miles away, most of us are going to order an Uber to get there because I'm not going to show up looking like a wet rat. But here's what Uber does. Uber knows you need us. And so they are charging you probably $40 for a ride that should cost you $15. It's a negative consequence. But in the moment, I'm like, this is the best answer. Just like your prospects in the moment are making the best possible answer for this moment in time but often aren't looking back at the negative consequences of that. And step number four is who else took a different approach? The line that I see in cold emails all the time that drives me nuts because we've all been told we have to do it is we helped this company solve the world's problems. Right? Like we did it. It was us. You are all here, probably not to hear from me, but probably to learn from each other. Right? It's why you come to events. It's probably why you're part of exit five community because you are very interested in knowing what do you know that I don't. Yet when we are in an outbound motion, our messaging style is to talk about ourselves and how awesome we are. When that's not often, particularly as you go more senior in the organization, what people care about. So there's an innate curiosity in what's everybody else doing that I don't know. So let's take those four things and let's put it together into an El Nino. Cold email. This is a cold email. Some of you will hate it. That's just the game. Right? The idea here is instead of pitching a product, which is what 99.99% of cold emails do. And by the way, you could use this on a phone. You can use this on LinkedIn. It's not specific to cold email. But most emails pitch a product instead of prompting that kind of perceptual curiosity to think differently about themselves. So here's how I wrote it. Subject line, super boring. Uber bill. Not sexy, but I'm like, did I get overcharged? Let me open it. Saw you commute to work in Chicago. Looks like Chicago gets about 119 rainy days a year. The average American owns 2.1 umbrellas. Yet only 5% of us remember to bring an umbrella on days it's supposed to rain. At this moment, what I'm trying to capture is like, are you in that 5% or are you in the 95%? If you're in the 5%, cool. We're never, you're never buying my raincoat anyway. Just want to get to who you are. When this happens, how often do you end up ordering an Uber? Thanks to surge pricing, we end up spending $40 for a ride that should cost us $15. Betty commutes to the loop from Bucktown. She found a way to cut her Uber bill by $200 a month. Are you open to hearing how she did it? Now, what am I not talking about in this email? Raincoat. There's no mention of raincoat because, as silly as this is, people don't buy solutions to problems they don't think are important. But in sales and marketing, often we pitch our solution in the hopes that it will make someone suddenly have this realization it's important. My intention of a message like this is to get someone thinking about their own behavior. Before I ask them to start thinking about me, like I want you to do the mental math because if you're only taking one Uber a month, you probably don't have a big enough problem to solve. You probably don't need it and that's okay. I am intentionally alienating people. Problem I see a lot with sales teams is we try to appeal to everybody. And that's why we end up talking about ourselves because we're like, I don't know how to talk about you, but I do know how to talk about my product. And so in the initial situation, our unhinged cold email, the buyer read that and thought, man, I click into it, this thing costs $100. That's too expensive. Now we flip the equation because whether you're spending $200 a month on Ubers or $100 a month or $150, that is always going to be more expensive than the one time 100. So it's the same product, but we change the messaging recognizing that we know an umbrella is going to cause a status quo problem. Just like in your businesses, you know that there's ways that your prospects are solving the problem today without you. They will win if we don't preempt this. And so these are the four questions we went through. This is genuinely an enjoyable exercise to do. I know sometimes spending time with sales is not enjoyable, but if you go through this together, you will have different perspectives. You will butt heads, you will bash together. But I've yet to work with an organization who has gone through these four questions and said, we're not better off on the other side thinking about our messaging by not having this. And so this is something again, we don't want to do in isolation. You want to get product leadership. You want to get sales in. The only way sales is going to give you time for this though is if you do step one. And if you help them understand that there is a problem we're solving here and it's what's in it for me. We all know that's like the love language of sales, who wants in it for me. That's you don't have to build as much new pipeline. And so what this is really about, if anyone's heard of the term cost of an action, is like in cold outbound in our messaging, we tend to lead with ROI. Like ROI by definition is a maybe. If you do something, which is the hardest part, you might be rewarded with a positive return. Might. Might not. That's a high risk. If outbound and pipeline generation was as easy as me blasting emails saying ROI to everybody, sales would be the sickest job ever. But I think we've all sent those emails and saw nothing on the other side because everybody else is sending those emails too. So instead I would argue there's absolutely a place for ROI. We need it. But job number one is the prospect has to decide they have a problem we're solving and we're solving now. They have to perceive that there's a cost of staying the same. Not a cost of doing nothing. Again, I can't reiterate this enough. They're doing something, but staying with that something. If they don't perceive that there's a negative consequence to that, it doesn't matter how shiny our ROI is. They're not going to buy it, particularly in an outbound motion. So my next and final zero dollar exercise is a really fun one. Again, cold email pervert. So what you're doing is you're asking everybody in the business, everybody on the sales team, or if you're feeling funky, do the marketing team as well. And say I want you to write a cold email to an account that you really want to win or expand on the expansion side. And I want you to create a shared Google Sheet. It's very free. And you ask them to write the name of the company, the name of the prospect, the prospect's title, their subject line, and their cold email. And then you bring everybody together and you ask them to stand up and read that cold email in front of the room. And then you ask everybody in the audience, all the other people that are there, to clock at what point they check the fuck out. And I will tell you, I've had so many clients do this. I do this when I do workshops. It is so fun because you can see it on the seller's face. I've had sellers stop and be like, you're clocking out right now, aren't you? Yeah, you are. Okay. But the reality is sometimes when we're writing and we're doing the job and it's just like so mundane, we're not actually thinking about this is what the person on the receiving end is hearing in their head. And so to solve a problem, first sales has to be aware that there's a problem. The old way of writing cold emails, again, I can't reiterate this enough. It worked in 2020, 2021 when like everybody had money to spend and we didn't have as much custom optimization, like all that stuff. Shiny object error is really making this stuff ineffective. And it's not that you just haven't uncovered the magic channel or the magic like template. It's not that it's we've got to go in recognizing that buyer status quo is going to win a heck of a lot more than we do if we're not preempting it with our message. So step one to get sales buy in. It is a powerful story to say we actually probably need to stop pushing so hard on new pipeline generation and fix this closed loss status quo problem we have get both of us looking at the problem the same way. That's the common enemy. Step two is now let's realize like we're actually contributing to it. The way that we are writing these messages, whether you're giving me a cadence or a seller is out there doing it on their own is making the problem worse. And until we do that stuff, sales is going to think like this is just how we sell. This is the way we've always done it. It's really hard to make movement. So that's why I focused on these two areas first because I think half the battle is just like, how do I get sales on the right page? So Tommy wants slideys. If you do, you can email me or I'm sure Dave will send them out. But I want to say a very sincere thank you. I know we've got a few minutes for Q&A. Thank you for welcoming me as a sales person. You got it. You got it. You got to go. You got to go. Yeah. So if you if you have a question, give it up for Jen. Yeah. Hey, thanks for listening to this podcast. If you like this episode, you know what? I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private community for B2B marketers at exit five and you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exit five.com. Our mission at exit five is to help you grow your career in B2B marketing. And there's no better place to do that than with us at exit five. There's nearly 5000 members now in our community. People are in there posting every day asking questions about things like marketing, planning, ideas, inspiration, asking questions and getting feedback from your peers, building your own network of marketers who are doing the same thing you are so you can have a peer group. Or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days so you can go and check it out risk free. And then there's a small annual fee to pay if you want to become a member for the year. Go check it out. Learn more. Exit five.com and I will see you over there in the community. Today's episode is brought to you by Converter. 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