Shopify VP of Product on Transforming SaaS to AI-Native and Building $100B+ Agent-Led Commerce Vanessa Lee E288

In this episode, Carlos Gonzalez de Villaumbrosia, CEO at Product School, interviews Vanessa Lee, Vice President of Product at Shopify, the engine of global commerce powering over $1.1 trillion in sales. As the most senior product leader at Shopify reporting directly to the CEO, Vanessa oversees the product strategy for a platform with a $165B+ market cap and recent 30% year-over-year revenue growth. A two-time YC founder, Vanessa brings a builder’s mindset to leadership, emphasizing the need for technical fluency and courage as a service when making high-stakes decisions. What you'll learn: AI-Native Playbook: How Shopify transitioned from traditional SaaS to agent-led commerce. Internal AI Evals: How to use LLM-based judges to grade and ensure product quality. Technical Product Leadership: Why staying involved in API details and technical cohesion is critical for senior roles. The Versioning Framework: The strategy Vanessa used to successfully push back and convince her CEO to version Shopify's API. Key Takeaways: Beyond the PRD: Shifting focus from rigid specs to training AI models for non-deterministic outcomes. Courage as a Service: How to leverage deep domain expertise to find your screw it moment and drive organizational change. The Founder Mindset: Maintaining autonomy and an experimental spirit within a 10,000-person global organization. Credits: Host: Carlos Gonzalez de Villaumbrosia Guest: Vanessa Lee Social Links: Find out more about Product School here Follow our Podcast on TikTok here Follow Product School on LinkedIn here

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Shopify VP of Product on Transforming SaaS to AI-Native and Building $100B+ Agent-Led Commerce Vanessa Lee E288 is an episode from The Product Podcast by Product School.

This episode is 46:49 long.

This episode was published on Mar 18, 2026.

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