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