The Positioning Fix: Why Great B2B Products Still Need a Story Buyers Can Repeat

Lenny opens by introducing April Dunford as the author of Obviously Awesome and a positioning expert who has led teams at seven B2B startups and worked with roughly 200 companies. He notes that when a B2B product is not doing well, the product may not be the problem; positioning may be. April's guest post on positioning remains one of his most popular newsletter posts.

Dunford explains that she studied engineering, then took a product marketing job at a startup. She was assigned to a product that was not selling well, and after the company repositioned it, the product took off and the company was acquired. That experience led her to become a repeat VP of marketing at a series of startups—seven in total, six acquired—and later to consulting, where she has focused on positioning for B2B tech companies, mostly growth-stage startups.

She says there is no single metric that proves positioning is broken because weak positioning hurts across the pipeline. People may not understand what the product is, marketing may not resonate, sales calls may take several calls before the light comes on, and deals may close only to churn when customers discover the product is not what they thought. Because the symptoms show up against the company's own baseline, they are hard to measure directly.

The fastest diagnostic is to listen to initial sales calls. Customers may ask the rep to back up and pitch again, may say “you're just like Salesforce” when the product is not, or may say they understand what the product does but not why anyone would pay for it. Those reactions are strong signals that the positioning is weak.

Dunford defines positioning as defining how your product is the best in the world at delivering some value that a well-defined set of companies care a lot about. It includes the alternatives to what you do, how you are different, the value only you can deliver, who cares about that value, and the market category you intend to win. She notes that positioning is an old concept but is often stretched into many different definitions, even among marketing leaders.

Weak positioning often comes from misalignment rather than from no one having the right answer. The founder, marketing, sales, and product may each have a slightly different version of the positioning, and that drift compounds. Dunford argues that positioning has to be built with marketing, product, sales, customer success, and the CEO in the room so that everyone brings their customer and product knowledge and leaves with agreement.

She says the majority of problems she sees are misalignment. In one common case, a founder can tell the story well but new senior hires cannot, so the founder hears the wrong pitch on sales calls and sees the wrong message in marketing. In the other, a company has grown quickly, the market has shifted, and the head of product or marketing sees that the company is positioned for the market it used to be in, but cannot get the founder and team aligned.

When positioning works, it feels obvious. Dunford points to Postman, now described simply as a platform for building and using APIs; the clarity looks inevitable, but it was not obvious before the work. Positioning also changes over time because products and markets change, so even good positioning can go stale and should be checked periodically.

Dunford warns against starting by asking everyone why customers love the product; that produces a pile of opinions. The first step is to identify competitive alternatives—what you have to beat to win a deal. In B2B, that means both the status quo, whatever the company is doing now even if it is a spreadsheet or an intern, and the short list of vendors the buyer would consider.

She stresses that the status quo should not be discounted. B2B companies lose about 40% of deals to “no decision,” which often means losing to the spreadsheet, pen and paper, or interns. If the positioning does not beat the status quo, the buyer will never come off it; if it does not beat the short list, the buyer will choose someone else.

Once the alternatives are clear, list the capabilities the alternatives do not have—product features, pricing, services, or company capabilities. Then translate each capability into customer value by asking “so what?” and group the answers into two or three value themes. Doing it this way ensures the value themes are differentiated rather than generally valuable things any competitor could claim.

Next, identify the characteristics of target accounts that make them care a lot about that differentiated value; those are the best-fit customers. Finally, choose the market category that makes the value obvious to those customers. Dunford summarizes the five parts as competitive alternatives, differentiated capabilities, differentiated value, best-fit customers, and market category.

Dunford uses Help Scout as an example. Help Scout sells customer success software into a crowded market where Zendesk is the gorilla, but it also competes with email or a rudimentary shared inbox. Its differentiation is a service-oriented shared inbox and a philosophy of treating customers like people—assigning a person rather than a ticket number, and offering chat only when a real person is available.

Mapped to value, Help Scout is not trying to push customers to low-cost channels; it is trying to deliver amazing customer service that deepens the relationship. That value matters most to direct-to-consumer and e-commerce brands for which customer service is a primary way to build loyalty, not to a phone company focused on reducing call-center costs. Those e-commerce brands are the best-fit customers for the story.

The sales narrative then starts with the idea that customer success is a growth driver for modern e-commerce companies. It contrasts Help Scout with alternatives that treat customers like a number and push them to low-cost channels, framing those alternatives as treating service as a cost center. That is how positioning becomes a story that clicks with the right buyer.

The output is not just a document. Dunford brings sales, marketing, product, customer success, and the CEO together to work through the five parts, then documents the positioning. But the team also storyboards a sales narrative and turns it into a pitch, deck, demo, and script so that sales can tell the story and the rest of the company knows how to tell it too.

Dunford says positioning should take the customer's viewpoint. In a typical B2B buying process, a VP wakes up with a problem and assigns someone—say John in sales ops—to find a CRM. John is not an expert on the CRM market, so he googles and gets a firehose of vendors, all claiming to be in the top right quadrant.

John has to make a short list and justify the choice to his boss. He cannot say he picked the red one or spun a wheel; he needs a reason that makes him look smart. The vendor's best move is to explain how the market shakes out—which tools fit enterprises, which fit certain situations—and then show why this buyer, with these characteristics, needs these four things that only this product has.

If the buyer cannot figure out how to justify the decision, the result is often no decision: keep the spreadsheet, delay the project, and lose the deal. That is why “we're better” is not enough; better has to mean a specific value for a specific type of customer. Better for a small company is not the same as better for a large enterprise.

Dunford distinguishes positioning from messaging and branding. Positioning is the fundamental input: it defines the competitive alternatives, how you win, where you win, and who the message is for. Messaging is usually the text on the homepage, and branding is what the brand should stand for; neither can be done well until positioning is clear.

She points to Magic Leap and Google Glass as examples of spectacular technology that initially lacked a clear so-what. The demos were mind-blowing, but it was hard to see who the target market was and what value the product delivered. Both later tightened their positioning around specific B2B use cases, such as manufacturing and other narrow applications.

The Segway is her archetype of a positioning failure. The founder had a strong track record, raised a huge amount from famous investors, and teased the product as a “revolution in human transport” without saying what it was. People expected flying cars; when the Segway appeared, the hype collapsed, and customers were left to decide what it should be compared to—a car or a bicycle.

Dunford says that refusal to position the Segway at a micro level made early users miserable because nobody knew where it was supposed to be driven. Cars honked if it was on the road, and pedestrians objected if it was on the sidewalk. The technology was ahead of its time, but without positioning to answer who it was for and why they should care, it failed.

Dunford believes most companies can do positioning on their own, which is why she wrote Obviously Awesome as a methodology. Companies typically call her after trying it themselves and failing because the executive team is too opinionated to agree, because they are about to make a big sales or marketing investment and want to nail it once, or because they want an expert as a security blanket. The actual exercise is a week-long sprint, with prep before and work after; companies doing it themselves often trap everyone in a room for a couple of days.

For very early-stage companies, she recommends documenting a positioning thesis rather than over-tightening it. The thesis says what you think you compete with, what is differentiated, what value only you can deliver, who will care, and what market you intend to win. But it is based on assumptions, and in her experience it is always partially wrong.

She uses a fishing-net analogy: you may believe you have built the world's best tuna net, but if you launch it as only for tuna and you are wrong, it fails hard. A better approach is to keep the positioning a little loose, let fishermen try it, and see what they pull up; you may discover the net is actually great for grouper. Once you see enough signal and a pattern in who loves the product and why, then you tighten the positioning and scale.

The trigger for tightening is the emergence of a pattern. Early on, companies often see all kinds of customers liking the product for all kinds of reasons; later, a thread appears—customers share a marketing automation tool, a sales-team size, or some other characteristic that predicts a good pitch. When the pattern comes into focus and you know you win under certain conditions, it is time to tighten positioning and step on the gas.

Dunford says segmentation and personas are poorly defined in marketing and often confused. Segmentation splits a market, and in consumer marketing it can look like a persona—for example, toothpaste for teenage boys who want a date. Personas are about people: the buyer's hopes, fears, and goals. In B2B, segmentation is usually about company characteristics, not individual buyer demographics.

B2B segmentation can use firmographics such as company size, revenue, and geography, but it can also use highly actionable patterns—say, companies with a creative team of more than three people, a certain budget, and a particular software package. That kind of segment lets marketing target campaigns and sales build a list. When Dunford talks about seeing a pattern in who loves the product, she means the kind of company, not just the person.

In a typical B2B purchase, five to seven people are involved in the decision. John in sales ops may be the person doing the research, but end users, IT, purchasing, legal, and security may all have a say. Marketing teams often respond by building personas for every one of those people, complete with stereotypes about their hobbies and communication preferences.

Dunford argues that the most important persona is the champion—the person who does the research, gets the short list, and builds consensus across the organization. If positioning does not resonate with the champion, the vendor never gets on the short list, so the other personas do not matter yet. Later in the deal, the vendor must arm the champion to sell IT, purchasing, users, and the economic buyer. She closes by pointing listeners to Obviously Awesome and dunford.com, and says she uses Twitter to sharpen half-baked ideas because people there push back.