Design Meets Business 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 – Intro
- 06:45 – Early lessons: creativity, writing, and how wayfinding shaped his design thinking
- 10:00 – The rise of AI in design: adoption phase, experimentation, and the gap between good and great
- 17:15 – What AI means for designers’ roles and careers
- 22:00 – How AI could empower design founders
- 27:00 – Deep thinking & using AI as a creative partner
- 40:20 – The future of design systems
- 47:30 – Craft, taste, and creating products with soul in an AI-driven world
- 55:00 – Building “real teams”
- 66:17 – End of show questions
Connect with J.B.
LinkedIn, Website
Selected links from the episode
AI-Generated “Workslop” Is Destroying Productivity
Real Teams, J.B.'s post