The Product Manager

Anneka Gupta, Chief Product Officer at Rubrik with prior leadership at LiveRamp, shares lessons from scaling multi-product portfolios across data protection, cyber recovery, and identity resilience. She explains why adding products multiplies complexity. She outlines when to build, how to allocate resources, how to organize teams, and a stack-ranking framework for prioritizing investments.

Amit Shah, COO at Virta Health and former industrial engineer, shares how an operations mindset helps scale a virtual metabolic health clinic. He talks about shifting from growth to scale, why simplicity gets harder as you grow, designing the clinician versus digital balance, org changes like squads over silos, and practical frameworks for using AI and data to preserve trust.

Rachel Wolan, CPO at Webflow with 20+ years in product leadership, talks AI-native product strategy. She covers how to evaluate AI opportunities, find defensible differentiation, and move prototypes to production with CodeGen. She also explores segmentation, build vs partner decisions, UX for nontechnical users, and preparing for answer engine optimization.

In this retrospective, Hannah and Becca explore 2025's major themes, emphasizing how product leadership navigated volatility and AI challenges. They discuss practical AI skills essential for product development and the importance of revisiting core management principles. Highlights include insights from CPOs on growth strategies, the necessity of admitting uncertainty in leadership, and the evolving landscape of buyer psychology. Looking ahead, they forecast conversations on ethical AI and workforce resilience for 2026.

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 newsletterConnect with Dhruv on LinkedInCheck out Dhruv’s website and Yutori

In this installment, Matt Graney, Chief Product Officer at Celigo with over 20 years in B2B product, unpacks the world of misleading product plays. He highlights the dangers of vibe coding and no-code illusions, emphasizing the gap between demos and production-ready solutions. Matt warns of AI's bias and stresses the importance of judgment and rigorous user research. He also shares insights from scaling Celigo's product team, and offers valuable lessons on prioritization and the sustainable use of AI in product strategy.

Chris Silvestri, founder of Conversion Alchemy and a conversion strategist with a software engineering background, dives into buyer psychology and AI's impact on marketing. He emphasizes that buyers prioritize outcomes over features and reveals common pitfalls in conversion optimization. The conversation unveils his MPG framework for effective messaging: Match motivation, Prove value, and Guide decisions. Chris also discusses the importance of context in delivering messages and how to balance machine-readable clarity with human connection in an AI-influenced landscape.

Maxine Anderson, Co-Founder and CPO of Arist, discusses her journey from teaching in rural Oregon to revolutionizing corporate learning. She emphasizes that traditional education hinders growth due to access and context barriers. Maxine highlights Arist's innovative text-based learning, using platforms like SMS, Slack, and Teams to meet learners where they are. She shares insights on the importance of concise content, tracking behavior change, and how AI enhances personalized learning experiences. Ultimately, she advocates that context and practice lead to true skill adoption.

Jean Castanon, Vice President of Digital Product at American Express, shares his insights from over a decade at the company. He reveals how his team quadrupled testing velocity, emphasizing an always-on approach to experimentation. Jean discusses redefining success metrics, building a dedicated experimentation team, and the importance of aligning teams towards a common goal. He also dives into Amex's innovative referral program and the role of AI in personalizing customer experiences and enhancing productivity, offering invaluable lessons for product leaders.

In this engaging conversation, Matt Wensing, Head of Product and Design at Customer.io, shares his insights on navigating the complexities of scaling organizations. He compares the challenges of startups to the tumultuous teenage years, emphasizing that this awkward phase is crucial for growth. Matt discusses the need for emotional intelligence in leadership, the importance of clear communication, and how to harness team potential through collaboration. He also introduces the OODA loop for better decision-making, encouraging a shift from founder-driven to distributed methods.