April Dunford on Why Sales Pitches Fail (And How Positioning Fixes Them)

The Hero's Journey Is Killing Your Sales

April Dunford has worked with roughly 250 companies on their positioning. Only one could explain the structure behind their sales pitch. The rest had decks that had "been around since the year of the flood," she says, with slides added and removed with each product release but no underlying logic. Or worse: no deck at all, just salespeople clicking through "12 dropdown menus" in a feature-by-feature product walkthrough.

The culprit? Marketers have been trained in storytelling frameworks that work beautifully for case studies and brand narratives but collapse in a sales context. "Marketers in general have been taught storytelling structures that don't work for sales," Dunford explains. The Hero's Journey—where the customer is the hero, encounters problems, meets a guide (you), and reaches the promised land—dominates marketing education. "This works really good for things like a customer case study," she says. "But for sales, sales needs a whole bunch of other stuff."

Sales isn't entertainment. It's evaluation. A buyer isn't asking "What's so great about you?" They're asking "Why pick you over the other guys?" That question demands a fundamentally different narrative structure—one that includes competitive framing, discovery, and market context. When Dunford published her second book, Sales Pitch, it was to solve a problem she kept encountering: companies would nail their positioning in her workshops, marketing would run with it, but sales teams would walk out asking, "How does that change my pitch?"

Most weak positioning comes from the different parts of the organization having slightly different ideas about those component pieces. The vast majority of software companies, when I walk in, if I ask product and sales, who do we compete with? I get totally different answers.

— April Dunford

You're Not Losing to Competitors—You're Losing to Indecision

Dunford repeatedly cites a statistic that haunts B2B sales: 60% of deals that start never finish. They don't lose to a competitor. They don't get an explicit "no." The ball just keeps getting kicked down the field until it rolls into a ditch of inertia and status quo.

The problem is that buyers aren't trying to understand your value in isolation. They're trying to map an entire landscape of alternatives, assess tradeoffs, and justify change to a committee of stakeholders. If your pitch is all about you—"Here's us. Here's the value we deliver. It's amazing. You should pick us"—you're not giving them the frame they need to make a decision. You're not painting a picture of the market and where you fit within it.

This is where deliberate competitive positioning becomes essential. Sales teams need to know not just what makes them different, but who they're positioning against. When product and sales can't agree on competitors, the pitch fractures. One team is selling against legacy spreadsheets, another against a well-funded startup, and a third is battling customer indecision without realizing it. No coherent story emerges.

Dunford's workshops are designed to force cross-functional alignment on the fundamentals: Who do we compete with? How are we different? What value can we deliver that no one else can? What does a good-fit customer look like? What market do we intend to win? "The trick is if we're going to get everybody together, we can't just put them all together in a room and be like, okay, why does everybody love our stuff?" she says. "There's gotta be some kind of a process or a methodology to work through that to the best of our ability takes the opinions out of it."

Positioning for VCs Will Wreck Your Positioning for Customers

Venture-backed startups face a unique positioning trap. When you're pitching investors, you want to define your market as "$8 zillion" and avoid niching down. You want to paint a vision of total addressable market domination. The whole world is your customer.

Then you close the round, turn to your first sales calls, and try to use the same pitch. "Your positioning for venture capitalists is going to be different than your positioning for customers," Dunford warns. "The two audiences have completely different definitions of value. They have different timeframes that they're thinking about."

VCs are buying into a long-term market thesis and your ability to execute. Customers are buying a solution to a problem they have right now, and they're comparing you to specific alternatives they already know. If you walk into a customer conversation with a VC pitch, you sound unmoored from their reality. You haven't defined who you're best for, what you're better than, or why they should care today.

Positioning defines how your product is the best in the world at delivering something, some value that a well-defined set of customers cares a lot about.

— April Dunford

The "well-defined set of customers" is the part that startup founders resist most. But it's foundational. Dunford's definition of positioning is precise: it's about being the best in the world at something specific for someone specific. That specificity is what venture narratives actively discourage.

Positioning Isn't Downstream from Growth—It's the Foundation

Dunford spent years as a VP of Marketing at companies like IBM and Nortel. Every time she joined a new company, the mandate was the same: "Go out there and do that lead generation thing." Her response was always a version of the same pushback. "If we don't make sure the positioning is solid first, then I'm just doing a bunch of stuff on top of this foundation made out of sand."

In her view, positioning isn't one lever among many. It's the substrate on which every other lever depends. "Almost everything we do in marketing and sales and growth has positioning at the foundation," she says. "We can't really figure a lot of this stuff out before we all get in agreement on, well, you know, who do we gotta beat in order to win a deal? And how do we win a deal?"

Her first move in any marketing role was to spend a couple of weeks hanging out with sales. Weak positioning reveals itself instantly in those calls. When a sales team can't articulate competitive differentiation, when prospects are confused about category fit, when deals stall for no clear reason—those are positioning failures, not execution failures.

This is why Dunford runs three-day workshops (technically half-days, because "people get really burnt out in these exercises"). Two days on positioning, one day translating it into a sales pitch. By the end, the entire cross-functional team—marketing, sales, product, CEO—has alignment on who they compete with, the value only they can deliver, their best-fit customer, and the market they'll win. Only then can growth tactics be deployed with coherence.

If the positioning is weak, then everything we do downstream is weak.

— April Dunford

Sales Pitch Is About Helping Customers Buy, Not Helping You Sell

Dunford opens her second book, Sales Pitch, with a clarifying sentence: "This isn't a book about selling, it's about helping customers buy." That framing inverts the typical sales playbook. Instead of optimizing for what the seller wants to say, it centers on what the buyer needs to know in order to make a decision.

Most B2B companies don't have a deliberate structure for their pitch. They have slides that accumulated over time, or they have no slides and just walk prospects through the product. Neither approach gives the buyer what they need: a clear sense of the competitive landscape, the tradeoffs between alternatives, and why this solution is the right fit for their specific context.

Dunford's structure borrows from her work at IBM, one of the only companies she's encountered with a repeatable sales pitch framework. It's designed to answer the buyer's actual question—"Why pick you?"—not the seller's preferred question—"Aren't we great?" It incorporates discovery, competitive framing, and market positioning in a way that most marketing-led pitch decks never touch.

The companies Dunford works with often have strong marketing teams that can take differentiated value from positioning and run with it. But sales teams walk out of positioning workshops, agree with the conclusions, and then struggle to translate them into a first call. The gap isn't in understanding the positioning—it's in the absence of a structure that maps positioning to storytelling in a sales context.

A buyer is not trying to answer the question, what's so great about you? The buyer is trying to answer the question, why pick you over the other guys? And the sales pitch has to answer that.

— April Dunford

Cross-Functional Workshops Are the Only Way Out

Dunford's methodology is ruthlessly cross-functional. She brings marketing, sales, product, and the CEO into the same room and forces them to agree on the fundamentals. If product thinks the competition is legacy enterprise software and sales thinks it's a hot new startup, no amount of messaging polish will fix the pitch.

"The only way to solve that is cross-functional stuff," she says. "Let's get everybody together." But throwing people in a room isn't enough. "There's gotta be some kind of a process or a methodology to work through that to the best of our ability takes the opinions out of it."

Her process is built to minimize opinion and maximize evidence. Who are we actually losing deals to? What do our best customers say when we ask why they picked us? What alternatives did they seriously consider? The answers to those questions reveal positioning—they don't require inventing it.

When the workshop ends, everyone walks out with the same answers. The same competitive set. The same differentiated value. The same definition of best-fit customer. The same market they're trying to win. And a sales pitch structure that maps all of that into a story buyers can use. "Now we're good," Dunford says. "Now we can go run everything."