Sketching with AI, Shipping with Care, and Avoiding Work Slop, with JB Chaykowsky (ex Intuit, now at Redpin)

J.B. Chaykowsky is a design and product leader with over two decades of experience spanning architecture, technology, and fintech. He spent more than 10 years at Intuit, where he led global design teams across the UK and France, shaping products for accountants and small businesses. Today, as Director of Creative & Design at Redpin, he’s focused on building a global real-estate payment platform that connects people across borders. Beyond his leadership roles, J.B. writes about creativity, design leadership, and the intersection of AI and craft—helping designers think more deeply, work with greater intent, and build products that reflect the people they serve.Timestamps:00:00 – Intro06:45 – Early lessons: creativity, writing, and how wayfinding shaped his design thinking10:00 – The rise of AI in design: adoption phase, experimentation, and the gap between good and great17:15 – What AI means for designers’ roles and careers22:00 – How AI could empower design founders27:00 – Deep thinking & using AI as a creative partner40:20 – The future of design systems47:30 – Craft, taste, and creating products with soul in an AI-driven world55:00 – Building “real teams”66:17 – End of show questionsConnect with J.B.LinkedIn, WebsiteSelected links from the episodeAI-Generated “Workslop” Is Destroying ProductivityReal Teams, J.B.'s post