About April
April Dunford is a positioning consultant and the author of Obviously Awesome, one of the most widely read books on product positioning in B2B. She spent years as a VP Marketing and CMO at a series of enterprise technology companies before going independent. She has since worked with over 200 B2B companies on positioning, from early-stage startups to companies approaching $100M in revenue. In 2026, she released a fully updated second edition of Obviously Awesome, seven years after the original.
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Most companies treat positioning as a one-time exercise. They do it at Series A, put it on the homepage, and move on. April Dunford has spent the last two decades cleaning up what happens next.
In this episode, we went deep on when to reposition, why deals go dark, and what most marketing teams get fundamentally wrong about competitive threats.
Here’s what I took away.
1) Your first wave of customers exists to invalidate your thesis, not confirm it. Every product launches with assumptions about who the buyer is, what the competition looks like, and what value the product delivers. Those assumptions are almost never right. April’s advice: keep positioning loose at the start so the market can pull you toward where you actually win. Tighten it only once the first wave has shown you where you were wrong.
2) Marketing teams change positioning because they’re bored, not because they should. April’s observation from running marketing teams: the team gets tired of the homepage at exactly the moment it starts working. Customers aren’t staring at it every day. The last thing you want is to change something that’s gaining traction just because the people closest to it have seen it too many times.
3) Don’t position against ghosts. In early 2025, April ran a positioning workshop with a company in the ITSM space. Their head of product insisted they needed to position against vibe coding tools. April’s question to the head of sales: has any customer ever mentioned it? Not once. Her position: if it’s not showing up in your deals, you don’t have to position against it. Following up a year later, it still wasn’t showing up. Monitor it. Don’t react to a threat your customers haven’t discovered yet.
4) 40 to 60% of B2B deals end in no decision. That’s a positioning problem. The data comes from a study of 2 million sales calls. In the majority of no-decision cases, the cause was indecision, not a preference for a competitor. Either all the solutions looked the same, or the risk felt too high. Both are positioning failures. The fix is sharper differentiation, clearer competitive framing, and a deliberate strategy to de-risk the purchase.
5) “Too expensive” usually means “too risky.” When customers say the price is too high, they often mean the commitment feels too large. April’s approach: break the deal into phases rather than drop the price. Let the customer prove the relationship before they have to bet everything on it.
6) Investor positioning and customer positioning are not the same document. Investors are evaluating a 10-year bet. Customers are solving a problem they have today. When a founding team comes out of a fundraising sprint and starts leaking investor language into the sales pitch, it confuses buyers who don’t share that time horizon and don’t care about the same risks.
7) Category creation is mostly magical thinking. Almost every company that has IPO’d in recent years competes in an existing category. April’s view: inventing a category name doesn’t mean you win it. The job of a market category is to orient the customer at a macro level. Existing categories do that work for free. New ones require you to explain the category before you can even begin the sales conversation.
Where to find April: https://www.linkedin.com/in/aprildunford/
Obviously Awesome: How to Nail Product Positioning so Customers Get it, Buy it, Love it (2026) : https://a.co/d/0eMZX1K9
Enjoy,
— Jordan
