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

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...