The Product Manager How to Navigate “Growing Pains” in Scaling Orgs (with Matthew Wensing, Head of Product and Design at Customer.io)
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Aug 19, 2025 In this engaging conversation, Matt Wensing, Head of Product and Design at Customer.io, shares his insights on navigating the complexities of scaling organizations. He compares the challenges of startups to the tumultuous teenage years, emphasizing that this awkward phase is crucial for growth. Matt discusses the need for emotional intelligence in leadership, the importance of clear communication, and how to harness team potential through collaboration. He also introduces the OODA loop for better decision-making, encouraging a shift from founder-driven to distributed methods.
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Two Jobs During The Transition Phase
- Scale-up roles require two jobs: deliver value and define how to deliver it.
- Employees should expect to help shape their role during the transition phase.
Test Autonomy With Bounded Ambiguity
- Give new hires slightly bounded, ambiguous direction and watch how they run with it.
- Use early days to test whether they thrive with autonomy or need more supervision.
Cement Strategy, Avoid The Telephone Game
- Strategy must be 'cemented' across levels to avoid reinterpretation.
- If people think "we can also do this," the chain of shared understanding is broken.