Design Meets Business

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 – Intro02:40 – Jennifer's journey from journalism to design08:26 – The three pillars: beauty, meaning, and wellness14:22 – Building culture that sustains craft28:16 – Why good debates and healthy conflict matter in design42:34 – Leading design in complex healthcare systems56:18 – AI's role in creativity and what it will never be good at01:04:12 – Presenting work and getting meaningful feedback01:06:44 – End of show questionsConnect with JenniferLinkedInWebsiteSelected links from the episodeHow 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 – Intro02:22 – Rachel's journey from photojournalism to design05:42 – The power of curiosity and being a generalist09:16 – Designing for infinity and infinite expressiveness18:34 – The tension between craft and efficiency in design28:22 – Material Design's impact and evolution35:48 – AI-powered search and building AI products at Expedia42:16 – The future of search and conversational interfaces48:24 – End of show questionsConnect with RachelLinkedInSelected links from the episodeExpedia in ChatGPTCarly 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 – Intro02:08 – Jehad's journey from engineering to design leadership05:32 – Being multilingual across disciplines and bridging gaps09:48 – Organisational design and how teams should be structured20:16 – The role of design systems and platforms at scale31:44 – Leading design in complex B2B environments42:22 – How AI is changing product building and design tools52:18 – The future of AI agents and conversational interfaces58:02 – End of show questionsConnect with JehadLinkedIn

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 – Intro02:26 – Vuokko's journey into design and joining Monzo06:16 – Building in the open and transparency as a core value11:42 – Scaling design whilst maintaining craft and quality23:12 – Building design culture and protecting craft at scale37:44 – Managing stakeholders and navigating disagreement48:36 – Transitioning from IC to leadership and learning to let go55:48 – Career development and focusing on strengths01:03:22 – End of show questionsConnect with VuokkoLinkedInSelected links from the episodeThe 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 arc06:45 – Taking risks and embracing discomfort13:20 – Reframing imposter syndrome18:40 – Balancing stability and growth24:50 – The importance of collaboration, improvisation, and jamming with others31:10 – Designing at the speed of conversation38:20 – Learning to let go: not every problem needs to be solved46:40 – Balancing collaboration with impact48:10 – Leading craft at scale54:00 – Reflections on growth, curiosity, and keeping design human72:38 – End of show questionsConnect with AndreaLinkedInSelected links from the episodeMidjourney11LabsKREA

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 Josh05:10 – How early experiences shaped his approach to creativity and experimentation10:25 – Breaking away from process16:30 – Jamming and working together23:00 – Iteration, failure, and confidence through experimentation29:40 – Designing for emotion and joy36:00 – Building psychological safety and low-ego collaboration42:20 – How design culture shapes product outcomes48:00 – Creativity outside of work and where inspiration comes from50:00 – AI as a design partner and what human context still mattersConnect with JoshLinkedInInstagram

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 – Intro05:10 – Lessons from working across hardware, software, and physical spaces09:20 – How curiosity and iteration shaped his approach to design leadership13:40 – Building design teams that collaborate across disciplines17:55 – The role of storytelling and empathy in influencing business outcomes22:30 – Designing for trust and simplicity27:45 – How Deel approaches product design33:10 – Balancing craft with speed38:20 – What good design leadership looks like in distributed teams43:00 – Reflections on curiosity, growth, and keeping design human55:34 – End of show questionsConnect with AviLinkedInSelected links from the episodeShape Up, by Ryan SingerMultipliers, by Liz WisemanTools Avi mentionedNotebookLMGenway AIBagel AIWhisk AIWeavy AIMobbin

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

Product and Design leader, Ryan Scott, discusses gaining influence and persuading stakeholders in design careers. He explores the importance of connecting design to business metrics, tailoring tactics to specific environments, and assessing team quality. Ryan also shares insights on his new business, Accelerate Design Company, and the benefits of mentorship and continuous learning.

Doug has been in the Design world for 30 years and is well known for his role as VP of Design at IBM, where he oversaw IBM's design practice, design career and leadership programs, and the scaling of cross-functional design thinking practices. Doug is a role model for many design leaders and someone I've been looking up to for many years. Having him on the show is such an honour.Timestamps:00:00 – Intro02:32 – The three chapters in Doug's career09:35 – Building good relationships at work13:18 – The environment needed for designers to do great work20:44 – The role coaching played for him and how he's coached others27:13 – How do you know when a report is ready for a promotion36:04 – An overview of the work done at IBM by Design 42:16 – The role of ethics in Design48:13 – Design in the age of AI51:04 – End of show questions.Connect with DougLinkedInSelected links from the episodeThis is a Prototype Podcast (Apple, Spotify, Google)The Making of a Manager, by Julie ZhouThe Total Economic Impact Of IBM’s Design Thinking Practice, by Forrester