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.

Resources from this episode:

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Check out Customer.io and Matthew’s website

Remembering US Olympic Coach Bela Karolyi: Michael's conversation with him in 2008