Olivia: A fascinating study cited in the book The JOLT Effect found that somewhere between 40 and 60 percent of all B2B sales deals end in… well, nothing. No decision. The customer just walks away. Jackson: Hold on, not that they lost to a competitor? Olivia: Exactly. They didn't choose someone else. They chose to do nothing at all. And that inaction, that paralysis, is the most fearsome competitor any business has. Jackson: Wow. That feels deeply, uncomfortably true. It explains so many ghosted emails and stalled projects. It’s the corporate equivalent of endlessly scrolling Netflix and then just going to bed. Olivia: It is! And it’s the exact problem at the heart of the book we’re diving into today: Sales Pitch: How to Craft a Story to Stand Out and Win by April Dunford. Jackson: April Dunford. I know that name. She’s a big deal in the tech world, right? Olivia: A very big deal. And she’s the perfect person to tackle this. She's not some ivory-tower academic; she's a legendary positioning expert who has been in the trenches, launching 16 products and consulting for over 100 startups. She’s highly acclaimed, and this book is a masterclass born from a very specific pain point she saw over and over. Jackson: What was that? Olivia: She would watch marketing teams craft this brilliant, sharp positioning for a product, and then see it completely die on the very first sales call. The story just wasn't making the leap from the marketing department to the customer's ears. Jackson: Oh, I’ve been on the receiving end of those calls. The ones where you can feel the life draining out of the room. It’s 45 minutes of someone just clicking through their own software, feature by feature, and you’re just thinking, "Why am I here? What problem does this even solve for me?" Olivia: We’ve all been there. And Dunford’s argument is that those pitches fail because they’re built on a fundamentally flawed premise about what selling even is.

Jackson: Okay, so what’s the big, flawed premise? That you need to have a slick, fast-talking salesperson? Olivia: Not even. It’s more fundamental. The flawed premise is that selling is the hard part. Dunford’s entire philosophy hinges on a radical, counter-intuitive idea: Buying is often much, much harder than selling. Jackson: Buying is harder than selling? That sounds backwards. The seller is the one trying to convince someone, facing rejection. The buyer just has to say yes or no. Olivia: That's what we think. But Dunford tells this incredible, and frankly hilarious, personal story that makes it all crystal clear. It’s the story of how she bought a toilet. Jackson: A toilet? Okay, I’m listening. This is not the case study I expected. Olivia: Right? She and her husband bought an old house in Toronto, and the contractor renovating the bathroom tells her, "Okay, you need to go buy a toilet. I need it by Friday." Simple enough, she thinks. She has zero experience with toilets. She walks into a specialty toilet store… and is just hit with a wall of them. Hundreds of toilets. Jackson: Oh no. I know this feeling. This is me in the cereal aisle. Olivia: Exactly. There are short ones, tall ones, round bowls, elongated bowls, dual-flush, single-flush, pressure-assisted… The first salesperson comes over and asks what she’s looking for. She says, "I don't know... a toilet?" He just shrugs and walks away. No help at all. Jackson: Useless. The classic "that's not my department" energy. Olivia: Totally. So she goes home and does what we all do: she starts researching online. And it gets worse. She’s reading reviews, technical specs, articles about "siphonic action versus washdown." She spends weeks on this. She gets so overwhelmed and frustrated that she finally decides, "You know what? Forget it. The old toilet is fine. We'll just keep it." Jackson: She chose to do nothing! The 60 percent! Olivia: She chose to do nothing! But then the story has a twist. She calls the contractor to tell him, and he says, "Too late. I already recycled the old one. I need the new one by Friday, or the whole project gets delayed." Jackson: He burned the ships! Now she has to make a decision. Olivia: She has to. So she drags herself back to the same store, completely defeated. But this time, a different salesperson comes over. And this guy is a guide. He doesn't ask what she wants; he starts teaching her. He says, "Look, there are basically three things to consider: quality, aesthetics, and the space you have. For quality, you want a Toto. They’re the best. Now, for your small bathroom, you'll want a round bowl, not an elongated one. And based on your style, I’d suggest one of these three models." Jackson: He narrowed the universe for her. He gave her a framework for thinking about the problem. Olivia: He gave her a framework! He made sense of the chaos. In fifteen minutes, she confidently bought a toilet and left feeling great about her decision. After spending weeks in a state of analysis paralysis. That, Dunford argues, is the essence of a great sales pitch. It’s not about selling; it’s about helping an overwhelmed customer make a confident decision. Jackson: That makes so much sense. Because the fear isn't just about spending money. In a business context, if you’re the person choosing the new software, you’re afraid of looking stupid. You’re afraid of it failing and getting you fired. As the book says, customers are "much less worried about missing out than they are about messing up." Olivia: Precisely. The B2B software purchase is just the toilet story with more zeros and higher stakes. An employee, let's call him Joey, is tasked by his CFO to find new accounting software. He does the research, gets a dozen demos. Every single one is a salesperson just walking through features. Joey gets more and more confused, more and more scared of picking the wrong one. So what does he do? Jackson: He recommends sticking with the old system. He does nothing. Olivia: He does nothing. Because it's the safest choice. And that's why the first job of a sales pitch isn't to talk about your product. It's to acknowledge the difficulty of the choice and position yourself as the expert guide who can bring clarity to the chaos.

Jackson: Okay, so if my job is to be that expert toilet guide, what does that actually sound like in a B2B pitch? How do you build a story that doesn't just devolve into a feature list? Because that seems to be the default for everyone. Olivia: It is the default, and Dunford argues it’s one of several common but deeply flawed approaches. There's the 'Product Walkthrough' we've been mocking. There's the 'Problem/Solution' pitch, which sounds good, but usually every competitor defines the problem in the exact same way, so it doesn't differentiate you. There's the 'Vision Narrative,' which is great for pitching investors about the future, but terrible for a customer who has a problem right now. Jackson: And the 'Hero's Journey,' which I've heard a lot about. The customer is the hero, you're the guide. Olivia: Right, but Dunford points out a subtle flaw. In those stories, the plan you give the hero is about execution—how to use the tool. It doesn't help them decide which tool to pick in the first place. It skips the most important part of the journey for the buyer. Jackson: So what’s the alternative? What’s the structure of a pitch that actually works? Olivia: Dunford’s framework is a narrative in two main phases. The first, and most important, is called "The Setup." It has three steps, and they happen before you even seriously introduce your own product. The steps are: Insight, Alternatives, and The Perfect World. Jackson: Insight, Alternatives, The Perfect World. That sounds more like a philosophy class than a sales meeting. Olivia: It kind of is! And that's why it works. You don't start with the customer's problem. You start with your unique Insight into the market. A point of view that no one else has. This establishes you as an expert. Then, you talk about the Alternatives. Jackson: You talk about your competitors? My old sales manager would have a heart attack. Olivia: This is the most brilliant part of the whole book. You don't bash them. You group them into approaches. You become the guide who maps the entire landscape for the customer. You say, "Look, to solve this problem, you can basically do it three ways. There's the 'Do-It-Yourself with Spreadsheets' approach. There's the 'All-in-One Enterprise Suite' approach. And there's the 'Specialized Tool' approach. Here are the pros and cons of each. Here's who each approach is good for." Jackson: Wow. So you're not saying 'our competitors are bad.' You're saying, 'the market is full of different tools for different jobs, let me help you figure out what kind of job you have.' That builds an insane amount of trust. Olivia: An insane amount. Because you're educating, not selling. You're helping them categorize their options. And once you've mapped the alternatives, you get to the third step of the setup: defining "The Perfect World." You basically summarize the ideal solution for a customer like them, based on the insights you've shared. You say, "So, for a company your size, in your industry, the perfect solution would need to be easy to use like the DIY tools, but have the powerful reporting of the enterprise suites, right?" Jackson: And if they say "yes"... you've basically already won. You've co-created the selection criteria with them, and it just so happens that your product is the only one that fits. Olivia: You've got it. That's the setup. Only after they agree on what the perfect world looks like do you transition to the second phase, the "Follow-Through," where you finally say, "Well, that's what we do." And you introduce your product and demonstrate how it delivers on that exact value. Jackson: Can you give me a real-world example? A company that does this well? Olivia: The book uses a great one: Help Scout. They entered the crowded customer service software market in 2011, going up against giants like Zendesk. A feature-by-feature pitch would have been suicide. Jackson: They would have looked like a cheaper, weaker version of Zendesk. Olivia: Exactly. So instead, their pitch framed the market. They'd start a call by asking, "So how are you handling customer support now?" The answer was usually one of two things: either a messy, shared email inbox, or a traditional help desk system like Zendesk. Jackson: The alternatives. Olivia: The alternatives. The Help Scout rep would then act as the guide. They'd say, "Yeah, we see that a lot. Shared inboxes are great for getting started, but they get chaotic and you can't track anything. Traditional help desks are powerful, but they're often clunky, and they treat customers like tickets to be closed, which can hurt loyalty." Jackson: They're outlining the pros and cons of each approach, without being nasty. Olivia: Perfectly. Then they'd define the perfect world. "What you really need is something that feels personal and easy like an email inbox, but has the power and automation of a help desk, all focused on creating a great customer experience." The prospect, of course, would agree. And only then would the rep say, "That's exactly why we built Help Scout." It positions them not as a competitor to Zendesk, but as a whole new category of solution. Jackson: That is so smart. It’s like you’re changing the rules of the game so that you’re the only one who can win. Now, I have to ask, because some readers have pointed this out—does this feel a bit... formulaic or repetitive when you read the whole book? Is the framework more complex than it needs to be? Olivia: That's a fair critique. The book does circle back to its core principles repeatedly. But I think Dunford does that intentionally. From her experience, if you don't give sales teams a very clear, repeatable structure, they will inevitably revert to the lazy, comfortable habit of just doing a product walkthrough. The structure isn't just for the customer; it's a discipline for the seller. It forces you to think about your value, your market, and your story in a rigorous way, every single time.

Jackson: It really all comes back to that idea of confidence, doesn't it? The old way of selling—the feature walkthrough, the high-pressure tactics—it creates confusion and fear in the buyer. And that fear is what leads to the biggest competitor of all: doing nothing. Olivia: Exactly. This new way, Dunford's way, is about building a story. And that story's entire purpose is to dismantle the fear and build up the buyer's confidence, piece by piece, until saying 'yes' feels like the most logical, safest, and smartest decision they can make. Jackson: So the takeaway isn't just a new set of slides. It's a fundamental shift in the goal of the conversation. Olivia: It is. Your job isn't to sell a product; it's to sell a decision. And you do that by telling a story that makes your unique value obvious. It’s a generous act. You’re giving the gift of clarity. Jackson: I love that. The gift of clarity. So for everyone listening, especially if you're in a role where you have to pitch ideas, products, or projects, here's a challenge. The next time you build a presentation, ask yourself this one question. Olivia: What's the question? Jackson: Does this story I'm telling help my customer make sense of the entire market, or does it just talk about me? Olivia: That's the perfect filter. It changes everything. And on that note, we'd love to hear your worst sales pitch stories. What's the most confusing, overwhelming, or just plain cringey pitch you've ever had to sit through? Share them with us on our social channels; we could all use a good laugh and a moment of shared pain. Jackson: I can't wait to read those. Olivia: This is Aibrary, signing off.