Podcast Summary: Positioning with April Dunford — "Post Positioning: Testing and Execution"

Host: April Dunford
Date: April 2, 2026
Episode Theme: Understanding the most effective ways to test, execute, and maintain product positioning after the core positioning work is done, with new insights pulled from the second edition of "Obviously Awesome."

Episode Overview

April Dunford shares hard-won lessons on what happens after a positioning exercise is completed. She digs into the realities of testing your new positioning, executing it within your sales and marketing teams, and maintaining its relevance as your company and market evolve. This episode is focused on the practicalities: how to validate positioning in a B2B environment, structure sales pitches, roll out new messaging, and avoid common pitfalls—all while emphasizing the importance of repetition and discipline in establishing your market identity.

Key Discussion Points & Insights

1. The Power and Challenge of Repetition in Positioning

• Repetition is Critical:
  • April opens by emphasizing that establishing a firm market position means delivering a consistent message—over and over—until you're almost tired of hearing it yourself.

    "At the point where you're quite sick of it is exactly where it's starting to land." (00:01)

• Inconsistent messaging creates confusion and dilutes brand impact.

2. The Gap in the Original Book — Testing Positioning

• Admitting a Past Oversight:
  • April confesses that the first edition of "Obviously Awesome" didn’t offer enough detail on post-positioning testing, assuming it was a “previously solved” problem.

    "I didn't really spend too much time on it because I thought these are previously solved problems ... And I think I was wrong." (03:00)

• She realized through practical experience and workshops that teams need more guidance here.

3. Why A/B Testing on Pages Isn’t Ideal for Positioning (Especially in B2B)

• A/B Testing Limitations:
  • Marketers often try to validate positioning by A/B testing landing pages, but this approach has many pitfalls:
    • It tests too many variables: Not just positioning, but also messaging, landing page design, taglines, calls to action, etc.
    • Unqualified traffic: Without control over who sees which page, it's hard to extract meaningful feedback relevant to your ideal customer.
    • Statistical significance challenges: B2B companies rarely have enough traffic for robust A/B results.

    "So A/B testing on pages, I thought that was kind of a non starter. So I don't think that's a good way to test your positioning." (06:44)

4. The Best Way to Test Positioning: The Sales Pitch

• Live Customer Conversations:

  • Instead, April strongly recommends testing positioning by embedding it into a new sales pitch and trying it out in real conversations with best-fit prospects.
    • Why this works:
      • You see real-time reactions, questions, confusion, and excitement.
      • You can ensure you’re talking to only your target customers.
      • The best reps can work and iterate the pitch for optimal delivery.

    "We should get marketing and sales to sit down together, take that positioning, translate it into a sales pitch, and then take your one or two sales reps ... and make those reps your best reps." (09:34)

    • After each pitch, debrief with the rep to tweak wording, diagrams, or objection-handling until both sales and marketing agree the pitch outperforms the old one.

• Passing the Test:

  • The moment your best sales reps prefer the new pitch over the old one, you’ve got a winner.

    "If I could give a rep a lot of time with it ... and eventually the rep says, you know what? I really like this pitch. I'm not going back to the old one. Now, you know, you got something." (15:48)

5. Sales Pitch Structure

• April’s Eight-Component Structure:

  1. Context/Insight: Share why your differentiated value matters and how you arrived at your approach.
  2. Competitive Alternatives: Analyze other market solutions and their ups/downs.
  3. Perfect World: Envision the “perfect” solution criteria with the prospect.
  4. Introduction: Present your product/company, including market category.
  5. Differentiated Value: Deep dive into your unique features/benefits.
  6. Proof: Use evidence, like customer examples, to back up your claims.
  7. Objections: Proactively address unspoken objections.
  8. The Ask: Conclude with a clear next step/request.

  "That's the structure I've been using forever. Because I think this is the best way to test positioning—translate it into a sales pitch and then test it." (24:18)

• April references her second book, "Sales Pitch," for those who need detailed instruction.

6. Rolling Out the New Pitch and Messaging

• Train with the Best:

  • Use the top reps who’ve already mastered and validated the new pitch to train others. Peer-to-peer sales training is much more effective than marketing-to-sales training.

    "Salespeople training salespeople instead of marketing people trying to convince sales that this is a good sales pitch—usually works way, way better." (31:15)

• Messaging Comes After Pitch Testing:

  • Don’t invest in rewiring all messaging until the pitch is road-tested and validated.

• Messaging Document:

  • Instead of updating the homepage immediately, create a reference messaging document (with boilerplate descriptions, taglines, feature language, approved graphics, bios, and quotes). This keeps downstream assets aligned and messaging consistent.

    "If you put everything together into a messaging document, then nothing can get more than one degree off that particular messaging document." (37:44)

7. Guarding the Positioning Against Drift

• Regular Check-Ins:

  • Positioning isn’t “carved in stone.” Regular market changes (like competitor acquisitions) or updates in your own product should prompt a review—a lightweight subcommittee (marketing, sales, product, CEO) can perform this every six months.

    "If anything big happens in the market, you should back up and look at your positioning." (41:10)

• Resist Tinkering:

  • Avoid changing positioning or messaging just because you’re tired of it. Only change when clear signals (from competitors, product, or customers) demand it.

    "We should resist the urge to monkey with positioning that's working." (51:20)

Notable Quotes & Memorable Moments

• On Repetition:

  "It requires you to essentially say the same thing over and over and over again until you're really quite sick of it. And at the point where you're quite sick of it is exactly where it's starting to land." (00:02)

• On Sales Training:

  "Sales training sales is a whole different thing... That usually works way, way better." (31:48)

• On Testing Positioning:

  "A much better way to test it ... is to take the positioning, translate it into a sales pitch, and do it in live customer conversations with a sales rep." (08:00)

• On Messaging Drift:

  "A year later, you've got messaging out there that doesn't look anything like the homepage anymore... If you put everything together into a messaging document, then nothing can get more than one degree off that particular messaging document." (37:55)

• On Reviewing Positioning:

  "I would have a positioning check in about once every six months ... and we'd say, 'Okay, competitive landscape. Has anything changed?'" (43:13) "If there's no need to change it, we should not change it and we should just leave it alone." (52:08)

Timestamps for Key Segments

• 00:00-03:00 — Repetition and discipline in messaging
• 03:00-08:00 — Why marketers A/B test and why it often fails
• 08:00-18:00 — Live sales pitch as testing ground; how to debrief and iterate
• 18:00-25:00 — Detailed structure of an effective sales pitch
• 25:00-32:00 — Rolling out the pitch: best practices in training
• 32:00-38:00 — Creating and using a messaging document
• 38:00-45:00 — Change triggers and the importance of positioning review
• 45:00-52:00 — How and when to re-evaluate positioning; fighting the urge to change too soon

Conclusion & Takeaways

April wraps the episode with a reminder:
Positioning is a living thing, requiring ongoing commitment, rigor, and care. Test your new position in the real world with trusted reps, stick to a disciplined rollout, and only revisit your core position when substantial evidence tells you it’s truly time to change.
Have a burning positioning question? April invites listeners to email her directly for future episode inspiration.

For entrepreneurs, marketers, and B2B leaders, this episode is a gold mine for practical execution after you’ve found your positioning sweet spot.