April Dunford is the positioning expert behind Obviously Awesome and a former repeat vice-president of marketing across seven venture-backed startups, most of which were acquired. Over the past decade she has advised roughly 300 B2B technology companies, all with sales teams, on how to position themselves against the competition. In this episode she joins hosts Lily Smith and Randy Silver to explain why so many companies are repositioning at once, how a strong point of view on the future underpins good positioning, and why the story a company tells about itself is a decision for product and sales, not just marketing.
Key takeaways
- Positioning is a company-wide decision, not a marketing exercise. Dunford's own experience repositioning a spreadsheet tool as an embeddable database shows how it reshapes pricing, sales motion and even the product roadmap, not just the words on a website.
- Major shifts such as the move to AI force widespread repositioning because customers no longer have a stable set of alternatives to judge value or price against, and both AI-native companies and traditional SaaS businesses are wrestling with where they now sit.
- Intercom's rebuild of its support product around Fin shows how staying anchored to the customer's underlying job, resolving a ticket, can guide a genuine AI-first redesign rather than a bolt-on feature.
- Companies need a clear, credible point of view on the future of their market, or customers facing genuine uncertainty will simply freeze and delay buying decisions.
- A compelling vision of the future has to flow from a company's real differentiated value, not be reverse-engineered to flatter its current position.
- Selling too far into a hyped future risks stalling deals, so the message needs a maturity model that shows customers a credible, low-risk path from where they are today to where the market is heading.
- Positioning should be revisited on a disciplined schedule rather than settled by whoever argues loudest in the room, and Dunford recommends a structured check every six months on competitors, differentiators and value themes.
- Customer advisory boards, quarterly executive account calls and a company's own sales team are the most reliable early-warning systems for shifts in budget, buying process and competitive threats, long before they show up as lost deals.
Chapters
- (00:00) Introduction to April Dunford
- (01:53) The story behind Obviously Awesome
- (05:33) Positioning as a cross-functional decision
- (07:23) Why everyone is repositioning right now
- (09:32) Intercom, Fin and the AI-native rebuild
- (11:53) Building a point of view of the future
- (16:52) Is the vision genuine or self-serving
- (18:00) How to develop your point of view
- (22:13) Stack Overflow, Salesforce and staying silent
- (23:45) Hyping the future without stalling sales
- (27:01) When positioning needs to change
- (28:42) Running a regular positioning check-in
- (30:29) Customer advisory boards and voice of customer
- (34:47) Predicting change after covid and AI
- (37:20) Wrap-up
