Design Meets Business

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

Ryan is the founder of Accelerate Design Company. He's a Product and Design leader who brought food photography, live-order tracking, and remote driver training to DoorDash, launched step-function improvements to Airbnb’s checkout, messaging, search, and host calendar products, and launched products at TechCrunch Disrupt, Dreamforce, and WWDC. Ryan has led teams of all sizes, from two to 200, and is now advising companies on product management, design, and go-to-market strategy, as well as helping mid-career designers develop business skills to do more influential work and have more meaningful careers.

Timestamps:

• 00:00 – Intro
• 02:39 – Ryan's career and his thoughts on design education
• 08:03 – Describing the ROI of Design – his course for designers
• 14:57 – Gaining credibility by connecting design to business metrics
• 24:17 – Tailoring tactics for your specific environment
• 28:28 – Pursuing stakeholders through building good relationships with them
• 30:45 – How does Design work at the different companies he worked 
• 39:00 – The befits of scrapping incremental testing
• 43:34 – Assessing the quality of a team before joining
• 47:15 – On Accelerate Design company, his new business
• 53:06 – End of show questions.

Connect with Ryan
LinkedIn, Accelerate Design

Selected links from the episode
Describing the ROI of Design, Ryan's course

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 – Intro
• 02:32 – The three chapters in Doug's career
• 09:35 – Building good relationships at work
• 13:18 – The environment needed for designers to do great work
• 20:44 – The role coaching played for him and how he's coached others
• 27:13 – How do you know when a report is ready for a promotion
• 36:04 – An overview of the work done at IBM by Design 
• 42:16 – The role of ethics in Design
• 48:13 – Design in the age of AI
• 51:04 – End of show questions.

Connect with Doug
LinkedIn

Selected links from the episode
This is a Prototype Podcast (Apple, Spotify, Google)

The Making of a Manager, by Julie Zhou

The Total Economic Impact Of IBM’s Design Thinking Practice, by Forrester

Dan is a seasoned designer with over 20 years of experience in leading teams at companies such as Farfetch, Just Eat, Wonderbly, and Fresha. Until very recently Dan ran a small design studio – Rubber Studio. In today's chat we get a behind the scenes view into the life of a studio owner, what's important when trying to find work, and how your life as a designer can change if you decide to start a studio yourself.

Timestamps:

• 00:00 – Intro
• 02:38 – Dan's journey into Design
• 05:43 – His thoughts on Design education
• 08:28 – His journey as a studio owner
• 19:44 – What you need to know before starting a studio
• 32:32 – What's important when pitching for work
• 43:39 – On his talk about innovation at Hatch Conference
• 46:36 – End of show questions

Connect with Dan
LinkedIn

Selected links from the episode
Chris Do
Just enough research, by Erika Hall
Supermensch: The Legend of Shep Gordon (Documentary Trailer)
Dan Tase: Why Innovation Fails? (And what can we do about it) – Talk at Hatch Conference

Dan is a seasoned design executive who's led teams at Microsoft, Google, UnitedHealth Group, Walmart, and Lloyd's, among others. From working on the Surface Tablet, starting Project ARA at Google, leading the efforts to redesign Walmart.com, and more recently writing his own book, Uplifting Design, Dan believes in the importance of Design at the core of any business, and that's what we're talking about today. We also chat in detail about how his design team has doubled conversion for walmart.com, and about why he believes that you should look at your career from a perspective of two year stretches.

Timestamps:

• 00:00 – Intro
• 02:42 – Dan's journey into Design
• 04:06 – Why Dan thinks Design is at the core of business
• 09:11 – The forces that come down to devalue Design
• 15:51 – Companies that show Design matters
• 23:24 – Designing software vs. hardware and how compassion fits into this
• 42:54 – On the redesign of Walmart.com
• 51:29 – Dan's new book, Uplifting Design
• 56:08 – Managing your career in two-year stretches
• 01:04:18 – End of show questions

Connect with Dan
LinkedIn, Uplifting.Design, Website

Selected links from the episode
Neol
McKinsey Design Report
Fuelling Creative Renewal Report

Lea is a Product & Growth Consultant with a massive proven track record of helping companies get traction. Today we talk about experimentation frameworks, how to build better relationships with Product, and about what kinds of designers are best to collaborate with.

Timestamps:

• 00:00 – Intro
• 02:36 – Lea's journey into Product
• 03:37 – On working for one company vs. consulting 
• 07:06 – Lea's definition of Product
• 10:50 – Building relationships with Product
• 19:18 – The ideal designer to work with
• 25:08 – On experimentation
• 47:39 – The importance of quality in a product
• 52:39 – End of show questions

Connect with Lea
LinkedIn

Maria is a Product Design Leader at Turo and Founder of Careercoach.design. In this episode get to talk about the rise of the Player-Coach Designer, about building better relationships at work, about coaching, and we also talk about practical advice on how to approach your job search. 

Timestamps:

• 00:00 – Intro
• 02:18 – Maria's journey into Design
• 04:28 – On Player-Coach Designers
• 12:43 – Maria's thoughts on Design leadership
• 19:21 – Building relationships at work
• 23:44 – Giving and receiving feedback
• 30:27 – Maria's practice as a Coach
• 34:10 – On finding a job
• 48:36 – Demystifying interview questions
• 54:24 – How to negotiate your salary
• 56:58 – End of show questions

Connect with Maria

LinkedIn, CareerCoach.Design

Selected links from the episode

Demystifying common design interview questions, by Maria 

Alastair Simpson is a design leader and mentor, serving as VP of Design at Dropbox. Prior to Dropbox, Alastair was Head of Design at Atlassian, where he helped scale the design team from 20 to over 250. On today's show we chat about craft and how important it is for designers at any level, persuasion, how to present work, and how to deal with puzzling feedback.

Timestamps:

• 00:00 – Intro
• 02:28 – Alastair's journey into Design
• 06:34 – On building the right habits
• 11:24 – Sharing work, getting feedback, and storytelling
• 27:45 – How to get good at presenting work
• 31:44 – Soft skills that are important for designers
• 33:56 – Craft of Design vs. surgical optimisation
• 41:29 – Leading through craft
• 47:16 – The importance of inspiring others
• 50:06 – What Alastair hopes will happen over the next decade
• 52:02 – End of show questions

Connect with Alastair

LinkedIn, Medium

Selected links from the episode

The one critical skill most designers overlook, by Alastair
Influence: The Psychology of Persuasion, by Robert Cialdini
Start With Why, by Simon Sinek
Atomic Habits, by James Clear

Sean has spent the past 25 years at the intersection of commerce, consumer behaviour, and data-driven feedback loops. This included working for Tesco, GfK, and two long stints with Amazon, among others. In this chat we talk about how design can better work with product, how to speak the language of our senior stakeholders, and what he's learned about hiring from interviewing over a thousand people at Amazon.

Timestamps:

• 00:00 – Intro
• 03:54 – How does Product act differently in small vs. in big companies
• 05:53 – Interviewing others as a Bar Raiser at Amazon
• 10:55 – Portfolios – How do you get to the bottom of study cases?
• 13:24 – The one question Sean likes to ask in interviews
• 17:58 – How does a good relationship between Design and Product look like?
• 29:58 – Challenges that Product faces when they deal with Design
• 49:10 – Making it 'cheap' to be wrong
• 53:23 – Why sometimes Design reports to Product
• 56:53 – End of show questions.

Connect with Sean

LinkedIn

Selected notes from the episode

Sean's 10 Product Development Principles (to create the right culture and velocity):
1. Solve the right user need
2. Measurable accountability to outcomes
3. Release value in slices (avoid long bets)
4. Put data in the hands of decision makers
5. Build once, run everywhere
6. Make it cheap to be wrong 
7. Build it fast AND proper
8. Extreme focus on top priorities
9. Simplify, simplify, simplify
10. Be credible

We're switching gears a little from Design and catch up with Tom Scott, who's sharing his thoughts on building and using your network for your job search, the rise of the player-coach designer, and his thoughts on design education.

Timestamps:

• 00:00 – Intro
• 03:52 – Community approach in recruitment
• 09:30 – The current state of design recruitment
• 13:56 – Portfolios – Do you need them?
• 23:04 – How to build and use your network for your job search
• 29:51 – The rise of the player-coach designer
• 36:51 – On design education
• 44:28 – End of show questions

Connect with Tom

LinkedIn, Verified, Verified Insights, Verified Insider Podcast

Selected links from the episode

Why You Shouldn’t Hire Junior Designers, by Christian Vasile