What happens when a single-product company decides to build a second—or a third—without unraveling the success of the first? The leap from one product to many rarely doubles the complexity; it multiplies it. Product leaders suddenly face sharper trade-offs: when to place bold bets, how to allocate finite resources, and how to distinguish between transformational expansion and slow erosion of a hard-won core. The challenge isn’t just growth—it’s protecting what already works while building what’s next.

Anneka Gupta, Chief Product Officer at Rubrik, brings hard-earned perspective from leading a portfolio spanning data protection, cyber recovery, and identity resilience, and from helping scale LiveRamp from an early-stage startup into a data connectivity leader. She shares the practical frameworks she uses to stack rank investments, the hidden cost of starving the core business in pursuit of innovation, and the lessons behind an acquisition that fell short of expectations yet unlocked unexpected opportunity. The result is a candid look at portfolio strategy in the real world—where focus, discipline, and clarity of intent matter more than ambition alone.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Anneka:
  • LinkedIn
  • Rubrik

Finding product–market fit isn’t the finish line—it’s base camp. In this episode, Hannah Clark sits down with Amit Shah, COO of Virta Health, to unpack what really happens after you’ve “made it” and the mountain suddenly gets steeper. Virta is scaling a fully virtual metabolic health clinic in a fast-moving healthcare landscape, and Amit brings a rare perspective shaped by nearly a decade inside the company—and a career that started in operations, not product.

Amit shares how Virta navigated rapid growth while building a scalable product organization, why simplicity becomes harder (not easier) as you scale, and how they make deliberate choices about where humans add the most value versus where AI should step in. If you’re wrestling with org design, prioritization, tech debt, or the ethics of AI in real-world products, this conversation offers a grounded look at what it takes to scale without losing your north star.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Amit on LinkedIn
• Check out Virta Health

AI has collapsed the gap between idea and execution—but standing out in a flood of generative tools requires more than just speed. Product leaders now face a different kind of challenge: evaluating opportunities with sharper questions, building for users with evolving expectations, and navigating distribution channels that look nothing like they did a year ago.

Rachel Wolan, CPO at Webflow, joins Hannah to unpack what it really takes to ship differentiated, production-ready AI products in a crowded market. Drawing from her experience leading product at Dropbox and now building an AI-native digital experience platform, Rachel shares how she approaches defensibility, user segmentation, AEO, and when to buy versus build.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Rachel on LinkedIn and Twitter/X
• Check out Webflow

Welcome to 2026! In this special retrospective episode, host Hannah Clark is joined by producer Becca Banyard to unpack the biggest themes, standout insights, and most listened-to moments from the past year. Together, they reflect on what made 2025 such a pivotal year in product—where AI reigned, volatility was the norm, and the role of product leadership was stretched in new directions.

This episode is both a reflection and a guide. Hannah and Becca break down what they learned from conversations with CPOs, founders, researchers, and consultants who all shared one thing in common: navigating change while building great products. Whether you’re a seasoned exec, a leader on the rise, or somewhere in between, this wrap-up points you to the episodes you shouldn’t miss—and gives a preview of where the conversation is headed in 2026.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Referenced Episodes & Guests to Revisit:
  • Finding Your Unfair Advantage in Product’s Wild West Era with Margaret-Ann Seger
  • How Did This CPO Pull Off 350% Growth in Two Years?! with Benjamin Berry
  • The Nuances of Product Leadership No One Talks About with Debbie McMahon
  • How to Adapt to the New Gold Standard in Product Management with Dr. Maryam Ashoori
  • The Product Leader’s Guide to Buyer Psychology with Chris Silvestri
  • The New Exec Playbook: Your Most Important First Moves in Your First Executive Role with Yue Zhao
  • Are We Overpromising and Under-delivering on AI? with Dhruv Batra
  • Why It’s So Hard to Adopt New Skills with Maxine Anderson
  • The Systems Thinking Process Used by the Most Adaptable Product Leaders with Sheryl Cababa

AI can solve Olympic-level math problems... and still fumble basic arithmetic. So what gives? According to Dhruv Batra, the answer lies in the “jaggedness” of intelligence—how AI can excel in some areas while completely breaking down in others. Dhruv, co-founder and Chief Scientist at Yutori, joins Hannah Clark to unpack the cognitive dissonance users feel when a model dazzles one moment and disappoints the next.

They explore how user expectations—shaped by decades of intuitive UI patterns and human conversations—often collide with the underlying limits of AI systems. From browser agents and automation to long-term feedback loops and trust-building, this conversation is a candid look at what today’s AI can actually do (and where it’s still bluffing). If you’re building with AI or trying to scope what’s possible, this one will recalibrate your expectations—in a good way.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Dhruv on LinkedIn
• Check out Dhruv’s website and Yutori

There’s a lot of smoke and mirrors in product right now—especially when it comes to AI. Shiny tools and slick prototypes are masquerading as production-ready solutions, and teams are feeling the pressure to keep up. But what happens when the hype outpaces the fundamentals?

Hannah sits down with Matt Graney, CPO of Celigo, to talk about bad product plays in disguise—from vibe coding and no-code illusions to AI-fueled shortcuts that chip away at real product rigor. With decades in B2B product and a track record scaling teams, Matt offers a sharp, grounded view on what’s actually changing, what’s staying the same, and how to keep your product sense intact through it all.

Resources from this episode:

• Subscribe to The CPO Club newsletter
• Connect with Matt on LinkedIn
• Check out Celigo

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 newsletter
• Connect with Chris on LinkedIn
• Check out Conversion Alchemy

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