April Dunford’s 1 Killer Question to Expose Weak AI Product Positioning
April Dunford, bestselling author of Obviously Awesome and one of the most trusted voices in product positioning, explains how to expose weak AI claims and anchor differentiation that wins deals.
TL;DR
April Dunford, the best-selling author of “Obviously Awesome” and “Sales Pitch,” joins LaunchPod to break down why most AI product positioning collapses when you take a closer look. She has spent 25 years as a startup executive and consultant, helping companies stop guessing and start winning. In a world where everyone states, “We have AI,” April explains how to expose weak differentiation and anchor your story in outcomes competitors can’t match.
In this episode, we cover:
Why positioning is a product problem and how undefined positioning leads to wasted roadmaps, “not good enough” feedback from Sales, and engineering teams burning out on features that don’t win deals
Why “we have AI” is no longer a differentiator, and what to focus on instead
The one killer question that instantly reveals whether a product’s claims are real
Why April loves when competitors lie, and how to ethically trap competitors who over-promise features
And finally, how to sell the “glorious future” without losing the deal you need to close today
1. Why most AI positioning sounds the same (12:20)
We’re past the phase where adding a chat interface or sprinkling AI into a roadmap turns heads. As April puts it, AI has become table stakes — and that’s exactly why positioning has gotten harder.
When every vendor says they’re “AI-powered,” buyers don’t hear differentiation. They hear noise:
“Just saying, ‘Oh, I got a chat interface for this thing.’ Who cares? Nobody cares. Everybody’s got one of those.”
What actually wins deals isn’t the presence of AI, but the specific value it unlocks — and whether that value is something competitors can’t deliver.
2. The killer question that exposes weak AI claims (16:42)
April explains that the fastest way to cut through vague positioning is to teach buyers how to pressure-test vendors themselves.
Rather than arguing feature by feature, the goal is to equip prospects with a simple question that reveals the truth behind the claim. When competitors overreach, the question does the work for you — and credibility collapses instantly.
“The right question is not why everybody loves us so much. The right question is: why pick us over the three other people on the short list and the status quo? What can we do for the business that they can’t?”
This is where strong positioning becomes a sales weapon, not a marketing slogan.
3. Why differentiated value beats AI features every time (15:00)
A recurring theme in this episode: companies often jump straight to talking about value without anchoring it in competitive reality.
The real question isn’t: “What value do we deliver?”
It’s: “What value do we deliver that others on the shortlist cannot?”
AI only matters insofar as it amplifies an advantage you already have — proprietary data, workflow depth, integration, or speed to outcome. Without that anchor, AI becomes interchangeable.
4. Positioning for now vs. Positioning for later (32:56)
April also tackles a tension product leaders feel every day: balancing long-term vision with short-term revenue.
“There’s things we’re worried about for the here and now, and then there’s things we’re worried about in the future. We might make a decision today that says, okay, today we’re positioned around this. That doesn’t necessarily mean that’s the way we win forever.”
Strong teams can hold both:
Positioning that wins deals today, against today’s competitors
A future vision that guides the roadmap without confusing the market
Blurring those two is how teams lose focus, burn out engineers, and stall sales momentum.
Links
Chapters
00:00: Introduction
01:45: April's journey from engineering to marketing to product positioning expert
06:47: The shifting landscape: Position from COVID to the AI era
08:23: Moving beyond "AI washing" to find differentiated value
17:45: Defining your true competitive landscape
22:20: How to be worth your customers' migration risk
25:58: Why April likes when competitors "lie" about their capabilities and features
32:05: Why positioning is critical for product and engineering alignment
36:05: April's new book details
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