In the world of B2B software, there’s a dangerous temptation to treat positioning like a checkbox: a workshop you run once, a tagline you set, and a “mushy” value proposition you leave on the homepage for three years.
But in a recent Business of Software AMA ahead of her talk at BoS Europe in Cambridge, positioning expert April Dunford made clear that even for the people who wrote the book on it, positioning is a living strategy that demands constant refinement.
As she prepares for her upcoming talk at Business of Software Europe in Cambridge, April shared why she decided to release an updated and expanded edition of her seminal book, Obviously Awesome.
The “Do-Over”: Why Even the Experts Refine Their Thinking
It has been roughly six years since the original release of Obviously Awesome, and in that time, the market (and April’s own perspective) has evolved. She noted that while the core framework holds true, working with dozens of more complex, multi-product companies has highlighted gaps in the original text.
“My thinking has changed on some things,” April admitted during the AMA.
“There are other things in the book that I really wished I had a do over on that I felt like I didn’t explain it well enough”.
She specifically pointed out that some concepts she originally glossed over deserved far more depth: “I went back to the book and went, Oh, man, I spent two pages on that, and it should have been 10”.
The Multi-Product Challenge: When Positioning Gets Complicated
One of the session’s central themes (and a question that surfaced repeatedly in the AMA) is how positioning changes when you’re no longer a single-product startup.
A bootstrapped UK e-commerce startup raised the challenge directly: they were serving three distinct customer groups (UK mid-market, UK enterprise, and an earlier-stage US market), each with different competitive landscapes. Should they position differently for each?
April’s answer cuts through the anxiety most teams feel in this situation. Start by mapping what customers would do if you didn’t exist (the “best alternative”) for each segment. Then ask what you offer that those alternatives don’t. The revelation that often follows: the differentiated value is the same across all segments, even when the competitors aren’t.
“It’s amazing to me how frequently we get to the value and it’s actually the same,” she said, sharing a story from her time at IBM. A product that served retailers and utilities seemed to require totally different pitches, until the team mapped the value. For Tiffany’s, the pitch was about keeping cash registers running. For Emerson Electric, it was keeping the lights on.
The underlying value, continuous availability across a heterogeneous back-end environment, was identical. One positioning, two sales conversations.
The exception, she explained, is when the value truly is different across segments. In those cases, you don’t have a messaging problem. You have a product strategy problem, and often a harder question: should you even be serving both markets?
Competing Against “Hand-Wavy” Giants
Another thread that resonated with the room: how do you position clearly when big incumbents are co-opting your language and claiming they do everything you do?
April’s guidance here is counterintuitive. The magic trick isn’t a new category name or clever tagline, it’s making the value gap undeniably visible. Don’t just explain what you do differently; help the buyer understand what that difference is worth.
She described a security company that spent all its marketing talking about its unique methodology. Their competitors responded simply by saying their own approach was “good enough.” The real answer wasn’t to double down on methodology, it was to reframe the conversation around outcomes: do you want 80% coverage, or 100%? If 80% is fine, here are your options. If it’s not, here’s why only one vendor can get you there.
For situations where the incumbent is already entrenched in an enterprise agreement, she was equally direct: “The value has to be huge. You’ve got to be able to measure it, sell it upward, and make your champion stick their neck out for it.” And sometimes the right answer is strategic segmentation — stop chasing the deals you’re never going to win (Microsoft shops, for instance) and focus energy where the incumbent’s hold is weakest.
The Hardest Part: Differentiated Value
If there’s one concept April wishes she’d given more space to in the original Obviously Awesome, it’s this one.
Most companies, when asked what their solution delivers, land on something vague: “we save people time,” “we reduce complexity,” “we improve efficiency.” But how much time? Doing what? And does anyone actually care?
“Differentiated value is a hard concept to get, and then it’s hard to get right,” she said. The updated book covers this in significantly more depth, and her Cambridge talk will dig into it further. Because, as she put it plainly: “It’s the keys to everything.”
April Dunford
Founder, Ambient Strategy
Differentiated Value: The Hardest and Most Important Problem in Positioning
Getting it right requires three things that are each difficult in their own way:
- Specificity. Vague value statements don’t win deals. “We save time” isn’t a position; it’s a placeholder. The goal is a tight, concrete, defensible claim, ideally one or two points, three at most. “If you can get it down to one, say it over and over until everyone is bloody sick of it, and then say it again for two more years.”
- Cross-functional alignment. Positioning done in a silo fails in execution. When the whole team (marketing, sales, product, leadership) works through the exercise together, they understand not just what the value statement is, but why it’s true. That shared understanding is what makes consistent communication possible.
- Discipline over time. The enemy of good positioning isn’t a bad competitor or a complex market. It’s boredom. Marketing teams get restless after six weeks and want to change the message. The whole point is to resist that impulse and stay consistent until there’s a genuine reason to revisit – a product change, a market shift, new competitive dynamics.
Landing and Expanding: Suite Positioning Done Right
For companies evolving from a single-product identity into a broader suite, April offered a framework that resonated with several AMA participants.
A compliance training company for healthcare organizations described the challenge: they’d spent ten years building a strong brand in a specific niche, and were now adding policy management, incident management, and patient experience tools. How do you expand the story without abandoning the equity you’ve built?
Her answer: don’t run from it. Use it as the anchor. The compliance brand is a strength, not a constraint, provided you can expand the definition of what compliance actually means. Instead of saying “we used to do compliance and now we do these other things too,” the more powerful move is to say: this is what compliance really means, and we’re the people who understand it better than anyone.
She pointed to Salesforce as a reference: they didn’t abandon their CRM identity when they built out the rest of the customer platform; they reframed the whole suite around “Customer 360” and kept the CRM as the anchor. Jury’s still out on how well that’s landed, but the strategic logic is sound.
Critically, she urged teams to resolve one question before tackling positioning: is the go-to-market strategy land-and-expand (lead with the wedge product, cross-sell later) or suite-led (introduce the full picture upfront and let buyers self-select)? Sales, marketing, and product often have different assumptions about this, and those misalignments surface in exactly the wrong moments – mid-deal.
A Note on AI and Early-Stage Positioning
Oh, you thought we wouldn’t talk about AI, right? April also weighed in on a question about OpenClaw’s rapid rise and whether good positioning even matters for early-stage AI products.
Her take: in the current AI market, you can generate significant short-term revenue with something novel and a compelling story, even if the story overpromises. There’s a captive audience of technically curious people willing to pay to “muck around” with something new. But she was clear-eyed about what that isn’t: a sustainable business.
Eventually, you’ll have to do the positioning work. You’ll have to answer who this is really for, what it actually delivers, and why it wins against the alternatives.
For bootstrapped founders in particular, she offered a simpler starting point: don’t over-engineer the positioning before you’ve learned anything. Put it out there, see where the market pulls you, and then tighten it down. The risk isn’t starting loose, it’s staying loose forever.
The Bottom Line
If the person who wrote the book on positioning feels the need to update her thinking after six years, that’s a signal to every founder and GTM leader: your positioning is not a static document.
The companies April described getting this right share a common discipline: They treat positioning as a strategic exercise that matures alongside their product, and they resist the temptation to mess with it just because the marketing team got restless. They get the cross-functional team in the room, do the work to find the real differentiated value, say it clearly, and stay consistent.
The ones who struggle mistake messaging for positioning, position the feature instead of the value, or let the internal desire for novelty erode the clarity they’ve built.
April Dunford takes the stage in Cambridge in April. If you’re attending BoS Europe, her session will be a direct look at where her methodology has shifted, and why those shifts matter for the complex, multi-product, enterprise-facing realities most B2B software companies are navigating right now. Join us.