Every product team faces the same monster: conversion optimization. But in 2025, the game has changed. With AI agents influencing discovery and AEO (Answer Engine Optimization) reshaping how people (and machines) interpret messaging, teams are now marketing to both human and agentic audiences.In this episode, Hannah Clark sits down with Chris Silvestri, founder of Conversion Alchemy, to unpack how product teams can use psychology and UX insights to craft messaging that drives both adoption and retention. A former software engineer turned conversion strategist, Chris explains how understanding human decision-making—and now machine reasoning—can help product leaders turn features into irresistible outcomes.Resources from this episode:Subscribe to The CPO Club newsletterConnect with Chris on LinkedInCheck out Conversion Alchemy
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Why It’s So Hard to Adopt New Skills (with Maxine Anderson, Co-Founder & CPO at Arist)
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 newsletterConnect with Maxine on LinkedInCheck out Arist
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How American Express 4x Its Experimentation Velocity in 1 Year (with Jean Castanon, VP of Digital Product at American Express)
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 newsletterConnect with Jean on LinkedInCheck out American Express
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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 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 newsletterConnect with Matthew on LinkedInCheck out Customer.io and Matthew’s website
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How to Balance Speed and Value: The Essential Role of Empathy in the AI Product Era (with Megan O'Rourke, Executive Director of Product at Metalab)
The Tin Man’s silk heart in The Wizard of Oz is a perfect metaphor for AI right now—it can convincingly mimic empathy, but it’s not the real thing. In this episode, Hannah Clark sits down with Megan O’Rourke, Executive Director of Product at Metalab, to explore the delicate balance between AI-powered productivity and human-driven resonance. They dive into why empathy and storytelling are irreplaceable in both product development and leadership, and the risks we run if we trade them away for efficiency.Megan shares stories from the field, frameworks for deciding when AI belongs in the workflow, and practical ways leaders can embed human connection into their teams’ processes. From reading the silence in a meeting to designing for emotional moments, this conversation is all about building products—and cultures—that people can truly connect with.Resources from this episode:Subscribe to The Product Manager newsletterConnect with Megan on LinkedInCheck out Metalab
Successful products don’t happen in a vacuum. Hosted by Hannah Clark, Editor of The Product Manager, this show takes a 360º view of product through the perspectives of those in the inner circle, outer perimeter, and fringes of the product management process. If you manage, design, develop, or market products, expect candid and actionable insights that can guide you through every stage of the product life cycle.
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