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 the true productivity metric. Subtraction as leadership. Farhan shares how founders and executives must delete outdated processes, rules, and layers of bureaucracy to make room for new ideas — why process should only exist if it makes something possible or 10x better. Hiring and growing AI-native talent. Why Shopify doubled down on internships, hiring 1,000 interns this year and next, and how younger engineers push full-timers to stay current by being born AI-native “centaurs.” Responsibility versus accountability. Why leaders can delegate tasks but not responsibility, and how to stay in the work without disempowering the team. Certainty as intolerance. Farhan’s reflection on why overconfidence kills creativity, and how leaders can replace fixed beliefs with wayfinding, curiosity, and adaptive decision-making. Rapid-fire reflections for CEOs. Ashok and Farhan close with lessons on showing unfinished work, modeling curiosity, and removing friction as a cultural operating system. Who Should Listen: Mid-market CEOs, COOs, and CTOs building adaptable organizations that can scale. Leaders focused on culture and transformation, not just technology adoption. Operators who want to apply product thinking and modern software practices to traditional industries. Notable Quotes: “We have a baseline expectation of using AI. If you have two people, one using AI and one not, they will both be evaluated the same.” – Farhan Thawar on AI usage expectations “We don’t like waste, but we don’t have limits. If you believe in your workflow, use the best model for your problem solving.” – Farhan Thawar on AI token cost and consumption “You can now buy directly in chat from Shopify merchants. That is a major shift in how people discover and buy online.” – Ashok Sivanand on Shopify launching all their merchants on ChatGPT’s Shop feature on the very day it was launched Related Reading and References: Shopify Blog: Shopify and OpenAI bring commerce to ChatGPT (official announcement) - https://www.shopify.com/news/shopify-open-ai-commerce?podconvergence Reuters: OpenAI partners with Shopify, Stripe, and others to expand ChatGPT integrations - https://www.reuters.com/world/americas/openai-partners-with-etsy-shopify-chatgpt-checkout-2025-09-29/?podconvergence TechCrunch: Inside Tobi Lütke’s AI Memo and Shopify’s Cultural Shift - https://techcrunch.com/2025/04/07/shopify-ceo-tells-teams-to-consider-using-ai-before-growing-headcount/?podconvergence Farhan’s opinions about token consumption - https://x.com/fnthawar/status/1930367595670274058 Farhan’s article about “looking stupid”- https://medium.com/helpful-com/why-looking-stupid-is-my-superpower-2ee3fe00a748?podconvergence The Convergence.fm first episode with Farhan in 2024 - https://convergence.fm/episode/from-code-to-culture-how-shopify-thrives-under-farhan-thawars-thought-leadership The Convergence.fm Episode about Tobi Lütke’s leaked AI memo mandate, and our 6 takeaways - https://convergence.fm/episode/shopifys-leaked-ai-mandate-explained-6-takeaways-for-your-product-team Tobi’s memo Tweet - https://x.com/tobi/status/1909231499448401946 Unreasonable Hospitality (book) - https://www.amazon.com/Unreasonable-Hospitality-Remarkable-Giving-People/dp/0593418573 Farhan’s Twitter (public handle) - https://x.com/fnthawar Reflection and Action Steps: Start with your mission. Before choosing tools, clarify what problem you are solving and what your business stands for. Enable your team. Ask whether you are removing barriers or creating them. Are employees empowered to experiment? Model the change. Use AI tools yourself. Share your learnings, wins, and failures openly. F Foster learning. Consider introducing internal forums or “thinking clubs” that encourage curiosity and reflection across your team.
