Observed Signal · Mar 10, 2026 · Content Publication · Source: Lennys Newsletter · Impact: 1/5 · Sentiment: Neutral

Advanced B2B Positioning Guide with April Dunford

Executive Signal Summary

Lenny’s Newsletter publishes an episode featuring April Dunford, a recognized expert on B2B positioning and author of Obviously Awesome. The conversation goes beyond basic positioning concepts to tackle four common roadblocks product teams face when defining market positioning and go-to-market (GTM) strategy. Topics covered include why cross-functional teams disagree on competitors, how to overcome product pessimism, applying the “So what?” test to clarify differentiated value, and using GTM decisions to inform positioning. The episode distills practical tactics for product and marketing teams to make clearer, more actionable positioning choices.

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High Confidence

Educational thought-leadership content on B2B positioning; useful for marketing/product teams but not a platform-level, policy, funding, or technical infrastructure development affecting AdTech at large.

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Key Takeaways & Evidence Grounding

  • April Dunford is the featured expert and is the author of the book Obviously Awesome.
  • April Dunford has spent roughly 10 years working with more than 300 companies on positioning.
  • The episode identifies four common positioning roadblocks product teams face when making positioning decisions.
  • The episode highlights the "So what?" test and the use of GTM strategy to drive positioning decisions.
  • Content was published as an episode on Lenny's Newsletter (lennysnewsletter.com).
Primary Source Grounding & Direct Attribution
Direct Origin Attribution
Primary Reporting: Lennys Newsletter•Published: Mar 10, 2026
Original Coverage Title: “A guide to advanced B2B positioning”

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Advanced B2B Positioning Guide by April Dunford

April Dunford (author of Obviously Awesome) provides an advanced guide to B2B product positioning, identifying four common, hard-to-see roadblocks—disagreement about competitors, product pessimism, poorly defined differentiated value, and unclear scope of what’s being positioned. She emphasizes using the prospect’s point of view, staying focused on near-term product capabilities, acknowledging the status quo as a primary competitor, and running cross-functional positioning workshops that include heads of marketing, sales, product, customer success and the founder. Dunford recommends grounding positioning in real sales evidence, exposing product teams to why they win, articulating specific business value buyers understand, and keeping differentiated messaging concise. The piece is practical guidance aimed at helping B2B teams align on go-to-market messaging and win more deals.

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