Turnaround Leadership with Matt Baer, CEO of Stitch Fix

What do you do when you inherit a declining company with brilliant people, a powerful mission, and a culture that never learned how to compete? And what if the very thing that could save it — human connection at scale — is the same thing the rest of retail has been quietly eliminating for thirty years? Matt Baer is the CEO of Stitch Fix, the AI-powered personal styling service that pairs algorithmic precision with real human stylists to deliver one-to-one retail experiences at scale. He joined Jonathan Kirschner, CEO of AIIR Consulting and host of A Podcast About Leadership, alongside executive coach and author Jamie Ramsden for a candid conversation about leading from the front — and refusing to take shortcuts. The Anatomy of a Turnaround — Baer walks through the three-phase transformation strategy he built at Stitch Fix: rationalize, rebuild, and return to growth — and why getting the sequence right matters more than moving fast. Retail Is a Competitive Sport — On the danger of complacency, Baer explains why the best retailers live in a state of perpetual transformation and how he worked to embed that fighting mentality into a company that was built more like a tech startup than a retailer. AI as Amplifier, Not Replacement — Stitch Fix's governing philosophy on artificial intelligence isn't about automation — it's about using AI to deepen the human relationship between stylist and client, not dissolve it. The Say-Do Ratio — One of the episode's most memorable concepts: why the gap between what leaders promise and what they deliver is the single clearest measure of trust — and how Baer used it to rebuild confidence with his team, board, and investors. Patience Is Concentrated Strength — Ramsden introduces a Bruce Lee-sourced framework for the hardest moment in any transformation: when the work is done, the system is in motion, and the results haven't shown up yet. If you're leading through change — or about to be handed a situation that demands it — this episode gives you both the map and the honest account of what the terrain actually feels like. The distance between strategy and conviction is where most turnarounds are won or lost. To learn more about how AIIR Consulting helps leaders build resilient, high-performing teams, visit aiirconsulting.com .