Every product manager obsesses over leadership styles, onboarding flows, and GTM strategies—but what if the biggest differentiator of success comes down to something much simpler? Learning. In this episode, Hannah Clark sits down with Maxine Anderson, Co-Founder and CPO of Arist, a text-based learning platform that flips traditional corporate education on its head.

Maxine started her career in rural Oregon classrooms, where she saw firsthand how inaccessible and ineffective most learning environments were. That experience sparked the idea behind Arist: meeting people where they already are, through tools like SMS, Slack, and Teams. What follows is a candid conversation about why more content doesn’t equal more learning, the real barriers that keep employees from growing, and how AI is reshaping not just education—but how organizations function.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Maxine on LinkedIn
• Check out Arist

Every product leader wrestles with the same tradeoff: move fast and risk breaking things, or move slow and risk irrelevance. But what if the real accelerator wasn’t cutting corners—it was systematizing experimentation? In this episode, Hannah Clark sits down with Jean Castanon, VP of Digital Product at American Express, to explore how his team quadrupled their testing velocity in a year, redefined what “success” in experiments really means, and built a referral program that became Amex’s second-largest global acquisition channel.

Jean brings over a decade of experience at Amex across strategy, marketing, and digital, and he shares how his team balances speed, scale, and sustainability in product strategy. From building experimentation muscle to future-proofing digital storefronts, this conversation is packed with lessons for product leaders at every stage.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Jean on LinkedIn
• Check out American Express

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:

• Subscribe to The Product Manager newsletter
• Connect with Matthew on LinkedIn
• Check out Customer.io and Matthew’s website