The Product Opscast Product Opscast Episode 8: Roadmapping: A Living Process
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Nov 12, 2025 Justin Woods, founder of Roadmap Heroes and seasoned product manager, shares insights on the art of roadmapping. He highlights common struggles companies face and outlines a strategic approach using the PIVOT framework. Justin emphasizes the importance of audience-centric roadmaps tailored to stakeholder needs. He warns against over-reliance on roadmaps, suggesting they should evolve continuously. The conversation also explores the role of Product Ops in fostering collaboration and the value of celebrating discovery, making roadmapping a living process.
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Dell Checkout Roadmap Example
- Justin recounts managing Dell's e‑commerce basket across 16 countries which demanded long-term strategic roadmapping.
- That role exposed him to regulation, payment changes and vendor coordination requiring a multi-year view.
Roadmap As Strategic Communication
- A roadmap is primarily a strategic communication artefact, not a feature list of promises.
- Justin Woods urges thinking in problems, ideas, value, outcomes and themes (PIVOT) rather than dates and features.
Roadmaps Reveal Organisational Maturity
- The roadmap often exposes organisational maturity and tensions between product and finance.
- Lack of cross-functional honouring of product empowerment creates persistent roadmap conflict.