The Product Manager

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.
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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.
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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.
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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.
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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.
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Check out Dhruv’s website and Yutori