#544 Reinventing Retail OS: Harish Chandramowli on AI, Workflows, and the Future of Fashion Tech

In this episode, Mehmet sits down with Harish Chandramowli, Head of AI at Good Day Software, to explore how AI is reshaping the future of fashion, retail, and e-commerce operations. Harish shares his journey from cybersecurity engineering at Bloomberg and cloud security at MongoDB to building fashion-specific AI tools that solve real operational pain points around data chaos, messy workflows, and inventory waste. This is a deep dive into verticalized AI, workflow automation, agentic systems, and the emerging category of Retail OS. If you’re a founder, investor, or tech leader curious about applied AI or the future of retail automation, this episode is full of insight. ⸻ 👤 About Harish Chandramowli Harish is the Head of AI at Good Day Software, a fast-growing platform redefining how fashion and retail brands manage operations. With experience at Bloomberg and MongoDB, he brings a unique blend of security engineering, data modeling, and real-world problem solving into the retail tech world. He previously founded FLA, a fashion operations startup, and now focuses on building AI-powered workflows and agents for e-commerce brands. Harish’s LinkedIn : https://www.linkedin.com/in/scharish/ ⸻ ✨ Key Takeaways • Why retail back-office operations are still broken and dominated by spreadsheets • The rise of Retail OS and why ERP is becoming outdated • Real examples of AI reducing hours of manual work • Why agentic workflows matter more than chatbots • The biggest unseen cost in e-commerce: data integrity failures • The hidden value of vertical AI models • How founders should think about AI “moats” • Red flags Harish sees in AI startup pitches • How non-technical founders can communicate with technical teams more effectively • Why everyone is on a level playing field in this phase of AI ⸻ 🎧 What You’ll Learn • How to build AI systems for operational workflows • Why fashion and retail create perfect environments for data-driven AI • How to spot real vs fake AI innovation • How AI can automate back-office processes like purchase orders, packing lists, and inventory reconciliation • Why agent-based AI is the future • How AI changes new-market entry strategies • How founders can pitch AI in a credible, non-hyped way ⸻ ⏱️ Episode Highlights (Timestamps) (For YouTube + Spotify chapters) 00:00 — Welcome and introduction 01:00 — Harish’s journey: cybersecurity, Bloomberg, MongoDB 03:00 — Why retail operations are still broken 04:30 — Discovering the back-office pain points in fashion 06:30 — The spreadsheet problem killing profitability 08:30 — Why e-commerce is a brutal margin business 10:00 — Workflow chaos and data fragmentation 12:00 — Retail OS vs ERP and what the future looks like 14:00 — How AI powers Good Day Software 15:00 — Chatbots vs real AI vs agentic workflows 16:00 — Automating packing lists, PO ingestion, and email workflows 17:30 — Agents detecting inventory discrepancies 18:30 — Using localized data for new market expansion 20:00 — Verticalized AI and the rise of industry-specific LLMs 22:00 — Accounting differences across regions 24:00 — What founders need to know about AI moats 26:00 — Why real-world data is a superpower 28:00 — Changing consumer funnels: search, ads, and GPT shopping 30:00 — From engineer to business thinker: Harish’s mindset shift 32:00 — ChatGPT as a tool for business communication 34:00 — The biggest red flags in AI startup pitches 36:00 — Why automating everything is dangerous 38:00 — Final thoughts on curiosity, experimentation, and the AI era 39:00 — Where to reach Harish ⸻ 📚 Resources Mentioned • Good Day Software https://www.gooddaysoftware.com/ • MongoDB • Shopify and e-commerce back-office operations • Vertical AI applications • Agentic workflows and email-based automation