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How to Navigate “Growing Pains” in Scaling Orgs (with Matthew Wensing, Head of Product and Design at Customer.io)

The Product Manager

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Startups don’t get easier with age—they just get more complex. Much like teenagers, scale-ups are constantly outgrowing their structures, still figuring out their identity, and not always great at setting realistic goals. But this awkward “in-between” stage isn’t a failure—it’s a rite of passage on the path to becoming a mature company.

In this episode, Hannah sits down with Matt Wensing, Head of Product and Design at Customer.io, who has seen scaling from nearly every angle: founder, product leader, and now executive. Matt shares how to bridge the gap between lofty strategy and day-to-day execution, why your org’s real capacity is often higher than you think, and how to turn constant experimentation from chaos into sustainable growth.

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Chapters

1. The Teenage Years of Growing Companies (00:00:00)

2. Leadership Challenges in the In-Between Stage (00:07:16)

3. Strategy Implementation and Avoiding Failure (00:14:58)

4. Creating Process from Success Stories (00:18:01)

5. Breaking Out of Failed Experimentation Cycles (00:26:05)

6. Testing People's Capacity and Decision Making (00:34:58)

7. Discovering Hidden Talent and Potential (00:43:41)

8. Closing Thoughts and Contact Information (00:45:35)

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