Grounded Product Management: Tech Debt, Internal Customers & Lessons from Southwest Airlines

• How should product leaders balance feature delivery, technical debt, and internal customers—before a crisis hits? Short answer (execution-first): Treat technical debt and internal tooling as first-class product investments. Make risk visible, quantify internal friction, build empathy for internal customers, and prioritize with multiple lenses (value, risk, and enablement)—not just shiny new features. In this Productside panel, Robyn Brooks hosts Joe Ghali (Productside) and Elad Simon (CEO, craft.io) to unpack what the Southwest Airlines operational meltdown teaches product leaders about scalable systems, neglected internal users, and the real cost of deferred investment. What you’ll learn (practical, not hype): • What technical debt really is—and why it’s unavoidable (but manageable) • How much sprint capacity to allocate to tech debt (and why “it depends” is real) • How Southwest’s outdated scheduling systems exposed hidden risk • How to convince leadership to invest in tech debt using impact, risk, and stories • Why internal customers deserve personas, journeys, and UX investment • How poor internal UX silently destroys velocity, morale, and margins • Quantifying internal friction: time lost, cost saved, and churn risk • Prioritization approaches that surface risk (WSJF, buckets, multi-lens scoring) • When dedicated internal-platform teams make sense • How empathy—not just data—changes executive decisions 280 Group is now Productside. Featured speakers: • Joe Ghali, former Principal Consultant & Trainer, Productside • Robyn Brooks, former Director of Product Management, Productside, and Wealth Management Specialist, Merrill Lynch • Elad Simon, CEO & Co-founder, Craft.io About Productside: Productside (formerly 280 Group) is an outcome-driven product partner helping teams build products that matter through training, consulting, and advisory services. Learn more: https://www.productside.com Follow Productside for more product leadership insights: Instagram:   / productside_   LinkedIn:   / productside   X: https://x.com/productside_ Facebook:   / productside