Cap Watkins was most recently VP of Product Design at Lattice, and previously he's held design leadership roles at Amazon, Etsy, BuzzFeed, and Primary.com. Cap started his management career as an experiment after experiencing bad management himself, deciding to do the opposite of everything he'd hated from previous managers. On today's show we chat about the basics of great management, why design lost its craft over the past decade, how senior ICs influence without authority, and how to make any project exciting enough to build your reputation.

Timestamps:

• 02:16 – Cap's intro
• 06:46 – Management basics: transparency, showing up, and treating people like adults
• 09:24 – Should you try management or stay on the IC track?
• 12:08 – How to avoid being a bad manager when you're starting out
• 19:24 – Building divisive opinions and culture through transparency
• 20:26 – How senior ICs influence without formal authority
• 25:40 – How design lost its craft and became too strategic
• 28:28 – The hiring crisis: from 1 in 10 to 1 in 100 pass rates
• 36:40 – Making boring projects exciting
• 44:14 – End of show questions

Connect with Cap
LinkedIn

Selected links from the episode
Managing Humans, by Rands
Turn The Ship Around, by Lt. David Marquet
The Making of a Manager, by Julie Zhou

Matt Davey is Chief Experience Officer at 1Password, where he's been for over 13 years, starting as a part-time contractor and growing alongside the company through multiple chapters of change. On today's show we chat about staying at one company for such a long time and what that means, the importance of self-awareness in recognising when your role has changed, why a healthy tension in a product team is important, how to make 'Good Trouble,' and how AI is reshaping Design.

Timestamps:

• 02:14 – Matt's journey at 1Password and growing with the company
• 04:42 – Recognising chapter changes at work
• 08:30 – The loneliness of design leadership and talking to peers
• 11:22 – Doing what you want to be doing and giving away responsibilities
• 17:48 – Storytelling and getting buy-in from execs
• 29:36 – Building products without much data
• 38:06 – Good trouble and healthy tension
• 54:06 – How AI is changing Design
• 01:07:32 – End of show questions

Connect with Matt
Website

Selected links from the episode
Making Good Trouble
What you can expect to work on as a 1Password intern
1Password Careers

Jennifer Darmour is VP of Design at Oracle Health, where she's reimagining the healthcare experience. Jennifer has developed a distinct point of view on design through three pillars: beauty, meaning, and wellness. On today's show we chat about building culture that sustains craft, why good debates lead to better design, how AI is reshaping creativity, and what designers should double down on.

Timestamps:

• 00:00 – Intro
• 02:40 – Jennifer's journey from journalism to design
• 08:26 – The three pillars: beauty, meaning, and wellness
• 14:22 – Building culture that sustains craft
• 28:16 – Why good debates and healthy conflict matter in design
• 42:34 – Leading design in complex healthcare systems
• 56:18 – AI's role in creativity and what it will never be good at
• 01:04:12 – Presenting work and getting meaningful feedback
• 01:06:44 – End of show questions

Connect with Jennifer
LinkedIn
Website

Selected links from the episode
How to argue using the RISA framework

Rachel Been is Expedia's SVP of Design. Previously, she was one of the designers who laid the foundations for Google's Material Design, and has worked across products at Airbnb, Google Home, and Nest. Starting her career as a photojournalist, Rachel brings a unique perspective to product design, grounded in curiosity and craft. On today's show we chat about designing for infinite expressiveness, the tension between craft and efficiency, the power of curiosity over specialisation, and what AI should and shouldn't be able to do.

Timestamps:

• 00:00 – Intro
• 02:22 – Rachel's journey from photojournalism to design
• 05:42 – The power of curiosity and being a generalist
• 09:16 – Designing for infinity and infinite expressiveness
• 18:34 – The tension between craft and efficiency in design
• 28:22 – Material Design's impact and evolution
• 35:48 – AI-powered search and building AI products at Expedia
• 42:16 – The future of search and conversational interfaces
• 48:24 – End of show questions

Connect with Rachel
LinkedIn

Selected links from the episode
Expedia in ChatGPT
Carly Ayres' essay on the great design reset.

Jehad Affoneh is Chief Design Officer at Toast, where he leads design across product, platform, and culture. Previously, he held design leadership roles at VMware and other complex B2B companies. Starting his career as an engineer, Jehad brings a unique perspective to design, viewing it fundamentally as problem solving. On today's show we chat about the transition from engineering to design, the value of being multilingual across disciplines, organisational design, and how AI is transforming the way teams build products.

Timestamps:

• 00:00 – Intro
• 02:08 – Jehad's journey from engineering to design leadership
• 05:32 – Being multilingual across disciplines and bridging gaps
• 09:48 – Organisational design and how teams should be structured
• 20:16 – The role of design systems and platforms at scale
• 31:44 – Leading design in complex B2B environments
• 42:22 – How AI is changing product building and design tools
• 52:18 – The future of AI agents and conversational interfaces
• 58:02 – End of show questions

Connect with Jehad
LinkedIn

Vuokko Aro is Chief Design Officer at Monzo, where she has led the design function for nearly a decade through hypergrowth from startup to one of the UK's most loved fintech brands. She oversees a team of over 100 people across product design, brand design, and user research. On today's show we chat about scaling design teams, building trust through transparency, the value of constraints, and how to focus on strengths rather than weaknesses as you grow in your career.

Timestamps:

• 00:00 – Intro
• 02:26 – Vuokko's journey into design and joining Monzo
• 06:16 – Building in the open and transparency as a core value
• 11:42 – Scaling design whilst maintaining craft and quality
• 23:12 – Building design culture and protecting craft at scale
• 37:44 – Managing stakeholders and navigating disagreement
• 48:36 – Transitioning from IC to leadership and learning to let go
• 55:48 – Career development and focusing on strengths
• 01:03:22 – End of show questions

Connect with Vuokko
LinkedIn

Selected links from the episode
The Monzo Book of Money

Andrea Mangini is a design and creative leader whose career spans some of the most design-driven companies in the world — from Adobe and Autodesk to Netflix and Shopify. She’s led teams that built the tools and experiences shaping how people create, design, and build. Andrea’s work focuses on design craft, leadership, and helping teams find courage in the uncomfortable parts of growth. She believes great design comes from curiosity, collaboration, and a willingness to keep learning, even when the path isn’t clear.

Timestamps:

• 00:00 – Intro and Andrea’s career arc
• 06:45 – Taking risks and embracing discomfort
• 13:20 – Reframing imposter syndrome
• 18:40 – Balancing stability and growth
• 24:50 – The importance of collaboration, improvisation, and jamming with others
• 31:10 – Designing at the speed of conversation
• 38:20 – Learning to let go: not every problem needs to be solved
• 46:40 – Balancing collaboration with impact
• 48:10 – Leading craft at scale
• 54:00 – Reflections on growth, curiosity, and keeping design human
• 72:38 – End of show questions

Connect with Andrea
LinkedIn

Selected links from the episode
Midjourney
11Labs
KREA

Josh is a super designer who believes the best ideas come from collaboration and play. Over his career, he’s worked across agencies and tech companies such as Google, ZOE, and Booking.com, helping teams find energy and originality in their process rather than following rigid methods. His approach to design blends experimentation, curiosity, and a love for building things together. Today, he sets the foundations for AI in Healthcare at Microsoft.

Timestamps:

• 00:00 – Intro and about Josh
• 05:10 – How early experiences shaped his approach to creativity and experimentation
• 10:25 – Breaking away from process
• 16:30 – Jamming and working together
• 23:00 – Iteration, failure, and confidence through experimentation
• 29:40 – Designing for emotion and joy
• 36:00 – Building psychological safety and low-ego collaboration
• 42:20 – How design culture shapes product outcomes
• 48:00 – Creativity outside of work and where inspiration comes from
• 50:00 – AI as a design partner and what human context still matters

Connect with Josh
LinkedIn
Instagram

Avi Ashkenazi is a design leader who’s spent his career moving between hardware, software, and strategy—always focused on how teams turn ideas into real products. He’s led design at global companies and helped build teams that work across both physical and digital experiences. Today, Avi leads design at Deel, where he’s shaping how millions of people get hired, paid, and supported around the world. His work is about creating simple, human experiences in complex systems and helping designers stay curious while scaling their impact.

Timestamps:

• 00:00 – Intro
• 05:10 – Lessons from working across hardware, software, and physical spaces
• 09:20 – How curiosity and iteration shaped his approach to design leadership
• 13:40 – Building design teams that collaborate across disciplines
• 17:55 – The role of storytelling and empathy in influencing business outcomes
• 22:30 – Designing for trust and simplicity
• 27:45 – How Deel approaches product design
• 33:10 – Balancing craft with speed
• 38:20 – What good design leadership looks like in distributed teams
• 43:00 – Reflections on curiosity, growth, and keeping design human
• 55:34 – End of show questions

Connect with Avi
LinkedIn

Selected links from the episode
Shape Up, by Ryan Singer
Multipliers, by Liz Wiseman

Tools Avi mentioned
NotebookLM
Genway AI
Bagel AI
Whisk AI
Weavy AI
Mobbin

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