Product Thinking Episode 255: How Shopify Is Leveraging AI at Scale with Vanessa Lee
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Nov 5, 2025 Vanessa Lee, VP of Product at Shopify, leads the charge in integrating AI for merchants, showcasing the AI assistant Sidekick. She discusses how Sidekick acts as a co-pilot, simplifying tasks like product creation and payment setup. The conversation reveals Shopify's partnership with OpenAI to boost product discoverability in ChatGPT. Vanessa explores the transformation of product management with AI, emphasizing the importance of aligning work with personal passions for a fulfilling career. Dive into the future of commerce and entrepreneurship!
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Sidekick As A Merchant Co‑Pilot
- Vanessa describes Sidekick as a co-pilot that knows Shopify and a merchant's business deeply.
- She recounts Sidekick creating products, collections, and helping set up payments on merchants' behalf.
Demos Hide Production Complexity
- Building a conversational assistant is easy to demo but hard to productionize due to unpredictable user queries.
- Vanessa emphasizes the difficulty of succeeding across every topic users might ask about.
LLM Judges Replace Traditional Specs
- Shopify built a synthetic-data pipeline using LLMs to simulate merchants and conversations for evaluation.
- They then created an LLM