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How Shopify Stays on the Bleeding Edge: AI, Culture, and Operating Like You'll Be Relevant in 20 Years (with Head of Engineering, Farhan Thawar)
Podcast: Convergence.fm (LS 31 · TOP 5% what is this?)
Episode: How Shopify Stays on the Bleeding Edge: AI, Culture, and Operating Like You'll Be Relevant in 20 Years (with Head of Engineering, Farhan Thawar)
Pub date: 2025-10-16
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In this episode of Convergence.fm, Ashok Sivanand sits down with Farhan Thawar, Head of Engineering at Shopify, to go behind the scenes of how Shopify not only keeps pace with rapid change but leads it.
The discussion explores how Shopify became one of the first platforms to allow merchants to sell products directly inside ChatGPT, why that move challenges Amazon's dominance, and what it takes to build a company that learns faster than it fails.
Farhan explains the systems that make being first repeatable rather than accidental, including Shopify's internal LLM proxy, MCP servers, experimentation culture, and democratized tooling.
If you are a CEO, COO, or CTO looking to scale through culture, systems, and intentional technology adoption, this episode shows what it looks like to operate with conviction and long-term relevance.
Key Topics and Moments: Shopify and OpenAI's commerce integration. The same day OpenAI enabled in-chat shopping, Shopify merchants were already live. Farhan explains what it takes for a company of Shopify's size to move with that kind of speed
Competing with Amazon through culture, not size. Shopify has 3,000 engineers compared to Amazon's 35,000+, yet continues to outpace bigger players by focusing on coherence, focus, and empowered execution rather than bureaucracy and scale.
The meaning behind Tobi Lütke's April AI memo. Farhan discusses how Shopify operationalized its "AI is non-optional" stance, what baseline expectations look like, and how performance is evaluated in an AI-native organization.
AI reflexivity and the "three buckets." Farhan explains how teams are taught to recognize "AI not allowed," "AI optional," and "AI mandatory" problems so that employees develop instinct for when to reach for AI — and when to pick up the screwdriver.
The risk of 'vibe coding' and why hand tools still matter. Farhan shares lessons from real incidents inside and outside Shopify, like the Cloudflare outage caused by unreviewed AI-generated code, and how engineering leaders teach judgment, not just prompting.
The LLM Proxy and MCP Servers. Inside look at how Shopify democratized AI across departments by building an internal platform that connects all major models and corporate data sources, enabling every employee to build workflows and ask intelligent questions — not just engineers.
AI budgeting vs. SaaS budgeting. Farhan explains why AI usage isn't treated like traditional SaaS spend and how Shopify encourages heavy experimentation by rewarding impact rather than punishing token consumption.
Experimentation as a system. How teams are encouraged to show work at 20%, not 80%, and why the speed of learning, not perfection, is t
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