Dive Club 🤿

James McDonald is one of my favorite visual designers on the planet… but recently he took on his first ever contract where he’s responsible for both designing AND building his ideas from scratch.

So I used it as an excuse to get him back on the show to learn his tactics for creating stunning web designs with Claude.

It’s a ton of screen-sharing and a heck of a behind-the-scenes into his process.

Some highlights:

- When James reaches for Figma vs. Claude

- How James builds custom mini d...

This week's episode is a behind-the-scenes of the Inflight design journey. So I invited my co-founder Kyle Barber (designer at Tinder, Facebook, and Airchat) to share what it's actually like designing a startup today.

Inflight Pitch Episode (the SPC pitch we mention in the fundraising section)

I’ve seen a lot of custom AI tools on this show…

But this week’s episode with Myles Palmer (Design Director at Metalab) might take the cake.

Myles is the perfect archetype for what it looks like to be curious as a builder today and in this episode he gives us the ultimate behind-the-scenes look at the internal tooling system he built at Metalab.

This week's episode is with Rhiannon Bell (VP of UX for Google Search) and we're doing a deep dive into what it takes to design for AI at the scale of Google.

Some highlights:

- The design decisions that unlocked AI Mode

- What it takes to design at the scale of Google

- Designing dynamic component systems for AI

- How AI is shaping the practice of design at Google

- What we can learn from the top designers at Google

- What skills...

This week's episode is with Danny Martinez and we're doing the ultimate deep dive into design hiring and what's happening in today's job market. Danny has the perfect vantage point as the CEO of Decimals—the platform that powers everything I do with the Dive Talent Network. So this episodes is about as practical as it gets.

- What companies want in a “design engineer”

- The biggest green and red flags from hiring managers

- How the best teams are iterating on the hiring process

- Examples of portfolios getting hired...

This week's episode is with Geoff Teehan—co-founder of the legendary design agency Teehan+Lax, longtime design leader at Facebook, and now Chief Design Officer at Lightspark.

Some highlights:

This week's episode is with Nev Flynn and we're doing a deep dive into how he's bringing artful expression into enterprise design as the Head of Design at ElevenLabs.

Some highlights:

This week's episode is with Ed Bayes and we're doing a deep dive into how designers at OpenAI prototype the future of Codex/ChatGPT Work.

Some highlights:

- How prototyping at OpenAI has shifted recently

- The design challenges of bringing Codex into ChatGPT

- How Ed thinks about the spectrum of dynamic interfaces

- How Codex thought about their information architecture bets

- Why Ed structures design teams around personas not features

- The traits of the designers making the biggest impact at OpenAI<...

This week’s episode is with Evil Rabbit who is the founding designer at Vercel and an iconic figure in the design community.

He shares his design journey (which started with his first job in Argentina at 12 years old)

So he’s going to share his journey in design and what it was like

Some highlights:

- What it takes to design an iconic brand identity

- How Vercel’s new Creative Studio team operates

- How he landed his first design job at 12 years old in Argent...

Grok Bot has been going viral the last two weeks so this week's episode is a behind-the-scenes of the design journey with John Bai (who was the first NYC design hire at Cursor).

He screen-shares a ton of agent interaction pattern ideas as well as his unused concepts for the Grok Bot onboarding flow.

Some highlights:

- The prototype that led to the Grok Bot mascot

- Why John realized chat was still the right UX for AI

- How John uses agents to streamline his Figma work

This week's episode is with Patrick Morgan and we're doing a deep dive into the prototyping environment he built for Sublime Security.

What started as an attempt to organize his team’s prototypes ended up becoming a new type of AI design tool. It's a great example of how designers can level up the team by building thoughtful internal tools.

Some highlights:

This week's episode is with Kyle Zantos who is officially the first person to make three appearances on Dive Club 🫢

Seems like AI totally transforms the design process every few months so Kyle and I play a little ping pong and share some of the workflows that we've been having success with lately.

This is easily one of the most practical episodes on the channel and hopefully you come out of here with some specific tactics you can add to your practice.

Some highlights:

- 5 use cases for designing with HTML doc...

Did you know Claude Design started off as a side project from one person?

That's what this week's episode with Nate Parrott is all about. He shares the origin story along with a ton of examples of how he's using Claude Design in his own workflow.

Some highlights:

- Nate’s tips for getting the most out of Claude Design

- Storytelling and communication tactics for designers

- How Nate views the landscape for design tooling today

- How “weatherman mode” turned into a killer voice mode

...

Charlie Deets (https://x.com/charliedeets) has designed Safari, Arc, and now Dia…

Needless to say he knows a thing or two about designing browsers 😅

So in this week’s episode Charlie shares the principles that guide his design practice and takes us on a tour of some of the finer craft details inside Dia.

Some highlights:

- Charlie’s tips for presenting design work

- How to protect your special sauce as a designer

- What makes Apple’s decision-making culture unique

- The differences...

Pablo Stanley (https://www.pablostanley.com/) has built as many creative tools as anyone in our industry.

So in this episode he gives us a behind-the-scenes of his latest creations (including how he prototyped the all-new design mode in Vercel's v0).

We go deep into:

- The two types of design builders at Vercel

- Pablo's approach to prototyping the new v0

- Behind the scenes of Pablo's custom design tools

- What historic artists teach us about AI and creativity

- How Pablo gets...

Jason Yuan (https://x.com/jasonyuan) has one of the most fascinating minds in design so naturally I like to keep tabs on what he is creating 😎

This episode is a deep dive into Jason Yuan’s creative process for Hivemind (his new social intelligence product).

He screenshares dozens of unused concepts, novel art directions, brand identities, and everything in between.

Some highlights:

- The journey of designing Dot

- Why Jason doesn’t believe in user research

- The surprising sources Jason uses for design inspo

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It kinda feels like how design operates at Anthropic is consistently 3-6 months ahead of the rest of the industry.

As a result, Meaghan Choi (https://x.com/meaghaneschoi) (Design Lead for Claude Code) has quickly become a staple guest on this show.

In today’s episode we go deep into her design process, how she uses the new Artifacts feature, how the shape of designer is evolving, and a lot more…

Some highlights:

- Designing experiences that don’t have UIs

- How Meaghan collaborates with Claude Tag

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Meng To (https://x.com/MengTo?lang=en) is one of the people I keep tabs on to see how he's evolving his workflow as he builds his ideas with AI.

So I sat down with him to get a look into what his process looks like now… (spoiler: he’s moved everything to Codex)

We do a ton of screen-sharing and go deep into his strategies for prompting, how to get better outputs from the models, and more 👇

Some highlights:

This week we are going behind the scenes of Config 2026 with Loredana Crisan (Figma’s Chief Design Officer) https://www.linkedin.com/in/loredanacrisan/

We talk about Figma’s vision for AI, why design is having “an identity crisis and a renaissance at the same time,” and what it means to use AI to express what’s already in your head (not outsource creativity to it).

It’s a clarifying conversation about taste, tools, and the future of design 👇

Some highlights:

- Designing systems not screens

- Loredana’s mental model for...

What does it look like when a designer with zero technical background commits to shipping something real?

That’s what this week’s episode with Brett Williams is all about.

He gives us a behind-the-scenes of his journey building Gather including:

This week's episode is with Ron Goldin who has led design at Google, Shopify, UberEats, and in my opinion... he's the perfect example of what it looks like to thrive as a design leader in an AI world.

So this week’s episode is a deep dive into his journey as a builder and it’s full of stories:

A couple of weeks ago I recorded my first ever episode in front of a live audience (at Ramp HQ in NYC) 🗽

So today I’m excited to share the panel discussion recording with 3 incredible guests:

It’s a deep dive into AI design workflows at Anthropic, Ramp, and Every and I think you’ll enjoy it :)

⭐️ Check out Andy’s course - Craft at Speed https://join.dive.club/maven-aff-andy-madrick

Use code DIVECLUB for 15% off

Andy Madrick ( https://x.com/andymadrick ) is rethinking what it means to be a designer in 2026.

While at Notion, he’s developed a workflow where he prototypes directly in code, ships frontend PRs, and uses AI tools like Cursor to own the final polish of user interfaces.

In this episode we get a look into how he keeps all these things in motion and still designs with insane attention to detail.

Some h...

Over the last few months, Tommy Geoco has went on site to study today’s top design teams (Vercel, Perplexity, Metalab, Ramp, etc.).

So this week’s episode is a deep dive into all of the trends he’s seeing around AI workflows and where design is headed next.

Some highlights:

How do the best designers shape strategy at companies like Shopify?

That’s what today’s episode with Design Director Katarina Batina is all about.

Some highlights:

Rafa Conde (https://x.com/rafahari) is a design engineer at Retro and one of the most creative designers I know. I still remember where I was when I first saw the video on his personal site (https://rafa.design/) 😂

In this episode we unpack what it means to design experiences that bring delight :)

Some highlights:

- Finding ways to introduce delight

- How to make users feel something

- The power of humor in your design

- How to lean into video as a superpower

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Imagine going from IC to leading the Wealthsimple design team in a few short years…

That was Polly D’arcy’s (https://www.linkedin.com/in/pollydarcy/) journey and today’s episode covers everything she’s learned along the way. We go deep into design leadership, craft, hiring, and a lot more.

Some highlights:

- Why Polly hires specialists over generalists

- Tactics to nail your next portfolio presentation

- What it looks like to lean into the moment with AI

- How Polly defines design quality at WealthS...

Capital, early Cash App, and most recently, X, all have one designer in common — [Brandon Jacoby](https://x.com/JacobyBrandon).

In this episode Brandon is talking about how he’s combining his years of experience designing with fresh, high-functioning teams and is now launching an all-new independent practice to help founders push past good enough.

He shares some really interesting thoughts on taste, being creative with AI, and how to thrive in a 0->1 environment.

Some highlights:

- The types of designer who get most amplified by AI

- What...

When it comes to tools and workflows, Brian Lovin (https://x.com/brian_lovin) is someone I pay very close attention to.

He’s actually the one who first got me hooked on Conductor (https://www.conductor.build/).

But times are changing (again 😅)…

So today’s episode is a deep dive into his design process and all of the ways he’s iterating on his approach to both using AI tools as well as building AI tools at Notion.

If you like getting into the weeds of how the best designers are wrangli...

If you're like me you gotta be curious... what's it like designing at OpenAI?

So I’m excited to share today’s episode with you :)

It’s a deep dive with OpenAI’s Head of Product Design, Ian Silber (https://x.com/iansilber).

Some highlights:

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- The traits of the best systems thinkers at OpenAI

- What makes the design culture at OpenAI unique

- The vision for OpenAI's dynamic interface library

- What it's like designing around chat as a primitive

- What...

Remember when the Carl Rivera (https://www.dive.club/deep-dives/carl-rivera) told us about his vision to create the new Shopify Product Design Studio?

Well in this episode I got to sit down with Marvin Schwaibold (https://x.com/MSchwaibold) from Molly studio who Shopify recently acquired to bring that vision to life.

We go deep into creativity, Marvin's journey with Molly, how he's building his ideas with AI, and a lot more.

Some highlights:

- How to become a well of creative ideas

- How AI unlocks how...

Flora Guo (https://x.com/floguo) has one of the more impressive career trajectories of anyone I've interviewed on this show.

She's currently the founding design engineer at Paradigm. But before that Guillermo (Vercel CEO) personally DM'd her to join the Vercel team.

So we're going deep into career growth, design engineering, what it's like being a founding designer at an AI-native startup.

- What it’s like being a founding design engineer at Paradigm

- The challenges of designing AI-first products that work at scale

- Flora’s expe...

Today's episode is with Kris Puckett who has led design at Mercury, Dropbox, and now as a design manager at Stripe.

His journey is the perfect example of what it looks like to lean into this moment in time with AI.

Some highlights:

- Behind the scenes of Kris’s Epilogue app

- How to create custom skills with Claude Code

- How to start building personal systems with AI

- How Kris taught Claude to be a metal shader expert

- Building internal tools an...

What does it look like to demonstrate uncommon care in the way you design and build an interface?

Josh Puckett has has spent nearly two decades designing products like Wealthfront, Dropbox and helping dozens of startups.

But recently he released Interface Craft which is a library of everything he's learned about through the years about designing with “uncommon care” 👇

⭐ Use this code for 20% off Interface Craft: DIVE20

Some highlights:

Today's episode is with Luis Ouriach (https://x.com/disco_lu) whose role as a designer advocate at Figma means he's constantly helping teams navigate this rapidly changing landscape... especially when it comes to design systems.

So we're going to do a deep dive into the trends he's noticing and what it all means for designers.

Some highlights:

- How design systems are changing with AI

- Luis’s ideas around agentic design systems

- Pitfalls to avoid when adopting AI with your team

- What trends we...

Today's episode with Cameron Worboys (Head of Product Design at Cash App) is an inside look at how an AI-native design org operates and the ways designers can thrive in this new world.

We go deep into:

Julien Martin's episode...

A few weeks ago, Stripe launched their [new site (https://stripe.com/) and reminded everyone who the 🐐 of web design is…

So I asked their Head of Design, Katie Dill (https://www.linkedin.com/in/katie-dill-79168b3) , to walk us through some of the tiny design decisions that make it so special.

But we also did a deep dive into how the practice of design is evolving at Stripe and everything they’re doing to push past the status quo.

Some highlights:

- How the “call for a new aesthetic” is influencing...

As software becomes easier to create than ever, what does it look like to truly differentiate with design?

Today's episode with Julien Martin (https://x.com/julienmartin_?lang=en) is an attempt to answer that question.

He was the Head of Design at Zenly, Snapchat, and Amo which is some of the most uniquely impressive consumer design I've ever seen.

Some highlights:

- Behind the scenes of early Amo explorations

- How the composition of design orgs is changing

- The unlock that led to Amo's unique...

Today's episode is with Tommy Smith who recently landed a new role as a part of the Dive Talent Network.

So we're doing a deep dive into what makes his portfolio so effective:

Ryan Stephen (https://x.com/Ryan__Stephen) is a product designer at Microsoft, but the reason I wanted to interview him is because he's the man behind some of my favorite design experiments on Twitter.

So in this episode Ryan gives us a behind-the-scenes look at his creative process, the tools in his stack, and how he approaches effective storytelling in design.

Some highlights:

- How Ryan sparks creativity

- The power of putting your work on Twitter

- How Ryan thinks about investing in his career

...