Jan 22, 2023 · 1h 5m · lennys-podcast
How to nail your product positioning | April Dunford (Obviously Awesome)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Positioning expert April Dunford breaks down her tactical five-step framework to help B2B tech leaders define differentiated value, align cross-functional teams, and drive sales. She details how to diagnose positioning flaws, avoid common buyer testing traps, and translate strategic positioning into high-converting sales narratives.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 12.9% of the talking time here. How this is scored →
Lenny as informed peer 1.3 Guest teaching 5.6 Guest disagreement 1.7 Lenny pushing back 0.1
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:01:30 Rant against standard marketing persona templates
Dunford forcefully denounces standard B2B persona exercises as a complete waste of time, rejecting conventional marketing orthodoxy in favor of focusing solely on the champion.
Hardest push from Lenny ▶ 35:55 Questioning whether differentiation is truly mandatoryLenny pushes back on Dunford's core framework by asking whether a product truly needs a clear differentiator or if simply claiming to be better can suffice.
Biggest teaching moment ▶ 59:30 Deconstructing multi-stakeholder B2B deal dynamicsDunford walks step-by-step through how enterprise purchasing decisions actually occur, demonstrating why treating peripheral committee members as primary personas completely fails.
Lenny holds their own ▶ 13:30 Extending positioning relevance to individual PMs and GMsLenny demonstrates domain knowledge by proactively expanding Dunford's positioning concept from broad executive marketing down to feature-level product management and business unit leadership.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| April Dunford's Journey into Product Positioning | 1 | 5 | 1 | 0 | Lenny opens by deferring entirely to Dunford's authority and asking for her career background. Dunford provides an expansive narrative of her transition from engineering to positioning expert and consultant. | |
| Unusual Client Examples: Twinmotion and Blue Light Analytics | 1 | 6 | 1 | 0 | Lenny asks how teams know when they have a positioning problem. Dunford details how weak positioning shows up as pipeline friction and confused sales calls, correcting the desire for a simple single metric. | |
| Defining Product Positioning and Its Core Elements | 2 | 6 | 1 | 0 | Lenny notes that positioning applies beyond founders to PMs and business unit leaders. Dunford expands on this by explaining that most positioning failures stem from internal misalignment across departments. | |
| Characteristics of Effective Positioning and the Postman Example | 1 | 5 | 0 | 0 | Lenny asks what successful positioning looks like, prompting Dunford to cite Postman as an example of positioning that feels simple and obvious. | |
| The Fallacy of Testing B2B Positioning on Non-Buyers | 1 | 6 | 4 | 0 | Dunford rejects the premise of judging B2B positioning based on non-buyer feedback, launching into a sharp critique of 'pitch the grannies' events at startup conferences. | |
| Step-by-Step Breakdown of the Positioning Framework | 2 | 7 | 2 | 0 | Dunford delivers a structured masterclass breaking down the five essential components of positioning, emphasizing that competitive alternatives must encompass status quo habits like spreadsheets. | |
| Sponsor Segment: Product Management with Productboard | 1 | 6 | 1 | 0 | Following a sponsor read, Dunford walks through a full real-world case study using Help Scout to illustrate competitive alternatives, differentiated value, and customer loyalty drivers. | |
| Translating Positioning into a Collaborative Sales Narrative | 2 | 6 | 2 | 1 | Lenny inquires whether distinct differentiation is strictly necessary to win. Dunford explains B2B buyer psychology, showing why differentiation is mandatory to prevent the customer defaulting to no-decision. | |
| Clarifying Differences Between Positioning, Messaging, and Branding | 1 | 6 | 2 | 0 | Dunford clarifies distinctions between positioning, messaging, and branding, using high-profile product failures like the Segway and early Magic Leap to demonstrate what happens when context is omitted. | |
| When and How Companies Should Execute Positioning Exercises | 1 | 5 | 0 | 0 | Lenny asks when companies should hire an external consultant versus running the exercise internally, and Dunford provides pragmatic operational timelines. | |
| Positioning Strategy for Early-Stage Startups | 2 | 6 | 3 | 1 | When Lenny suggests Dunford only works with late-stage companies, she corrects him with 'yes and no' and explains why early-stage startups should keep positioning loose as a thesis rather than over-tightening. | |
| B2B Segmentation vs Personas and Champion Prioritization | 1 | 8 | 5 | 0 | Lenny asks about segmentation versus personas. Dunford delivers a passionate critique of conventional multi-persona templates, arguing that B2B positioning must focus almost exclusively on arming the internal champion. | |
| Connecting with April Dunford and Using Twitter for Feedback | 1 | 1 | 0 | 0 | Standard wrap-up where Dunford explains how she uses Twitter as a sounding board to test raw ideas against constructive pushback, followed by mutual appreciation. |
Statements from this episode (22)
Dunford: Half of dental procedures fail due to terrible equipment
“Half the stuff that a dentist does in your mouth is very likely to fail because the equipment is terrible and the way they actually do things like cure fillings is actually really terrible.”
Dunford: Weak product positioning degrades metrics across the entire sales pipeline
“Weak positioning kind of gets you all the way across the pipeline. You know, it's weak positioning hurts you in the early stages of the pipeline and that, you know, people don't really get what you are, so they're not responding to your marketing the way They …”
Dunford: Initial sales calls reveal weak positioning when prospects get confused
“In sales calls, like particularly in an initial sales call with a client. And what you'll hear is things like the customer comes on, your sales rep comes on and your sales reps like doing a great job pitching the product. Like, oh, we got this thing and it doe…”
Dunford defines positioning: differentiated value for a well-defined target audience
“Positioning defines how your product is the best in the world at delivering some value that a well-defined set of companies care a lot about.”
Dunford: Positioning must be a cross-functional exercise across executives, sales, and product
“If we're going to fix this thing, we can't just have the marketing department or just the product managers sit down and cook up new positioning and then heave it over the wall to everybody else. It actually needs to be a group effort. It's a team sport. So if …”
Dunford: Internal misalignment causes most positioning problems, not lacking a story
“A lot of times it's misalignment. I would say the majority of the time it's misalignment because what it is, is like a piece of the company has it right, but the other pieces don't.”
Dunford: Really great product positioning feels obvious to customers
“When it's working really well, it feels like magic and really great positioning feels obvious. You know, you pitch to people and they're like, well, of course that's it. Like what else can it be?”
Dunford: Product positioning is not static and degrades over time
“Positioning is, is, you know, somewhat like messaging in some ways in that it's not a static thing. Like it changes over time. Like your product itself, it doesn't stay the same. The market doesn't stay the same. And so things will shift over time. And so you …”
Dunford: The only valid test of B2B positioning is pitching qualified prospects
“The true test of whether the positioning is working or not is if I'm sitting across from a qualified prospect and I tell the story, does the prospect get excited and want to buy something? That's the real test of it.”
Dunford: Startup pitch competitions judged by laypeople infuriate her
“Every year they have this thing and it's called pitch the grannies. And you go in and you're startup and you pitch the grandmothers and the grandmothers decide whether or not your pitch was any good. And this infuriates me because I'm like, This is a terrible …”
Dunford: Positioning must start by defining what you must beat
“So I actually think the first step in a good positioning exercise is to really understand what do we have to position against? So put another way, it's like saying, what do I have to beat in order to win a deal? So in positioning work, we call this competitive…”
Dunford: B2B companies lose roughly 40% of deals to 'no decision'
“In B to B, we lose about 40% of our deals to quote unquote, no decision, which actually means we lost to the spreadsheet. We lost a pen and paper. We lost to interns.”
Dunford: The best market category makes differentiated value obvious to target buyers
“The best market category is the context I position my product in such that this value is kind of obvious to these people.”
Dunford: Sales reps will invent their own pitches if given no story
“It's super important in sales, because if sales can't tell the story, they can't pitch it. If they can't pitch it, they're gonna make shit up.”
Dunford: Marketing and sales activities flow downstream from positioning
“So I need to have positioning figured out first, and then practically everything I do in marketing and sales flows downstream from that.”
Dunford: Unclear product positioning forces customers to guess its purpose
“And the interesting thing about this segue was that refusal to position it at a micro level left it up to the customers to decide what it was. So even when we saw it was like, okay, so it's human transport. We get that. But like, what should I compare it to? S…”
Dunford: Most companies can execute product positioning internally without consultants
“I think most companies can do positioning on their own. Like that's kind of my belief. Some companies I think lack the, you know, lack of methodology to follow to go do it. And so I wrote a book called Obviously Awesome, and that was the purpose of that book. …”
Dunford: Pre-launch positioning theses are partially incorrect 100% of the time
“And in my experience, 100% of the time, the thesis is partially incorrect. It's based on a bunch of assumptions and our best guess at it based on what we did in customer discovery or all our research we did before we built the thing, but we're never a hundred …”
Dunford: Early startups should keep positioning loose to find unexpected demand
“And so in these cases, I actually think it's better in the early days of a product to keep the positioning a little bit loose and allow the market to pull you maybe in a direction that you didn't think it was going to.”
Dunford: Enterprise software purchases typically involve five to seven decision-makers
“In a typical B to B purchase process, particularly if it's what we would call enterprise software, even if it's not very expensive enterprise software, typically we have between five and seven people are involved in, in what we call making the decision for wha…”
Dunford: Marketing personas are a waste of time except for the champion
“I think there's really only one persona that really, really matters in this. Which is the champion in the account, and we should be very thoughtful, and we should really have our arms around that persona. And then, later in the deal cycle, we need to figure ou…”
Dunford: Twitter sharpens thinking via pushback, whereas LinkedIn offers superficial praise
“Like if I have a half-baked idea, I throw it out on LinkedIn and everyone goes, that's great, April. And that's it. Whereas if I have a half-baked idea and I throw it out on Twitter. People aren't shy about telling me I'm wrong. And I appreciate it because I k…”