Dive Club 🤿

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

...

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

...

Today's episode is with Hannah Hearth who recently became the Head of Product Design at Vercel. We talk about all of the changes that are happening in our industry and what it all means for designers. Everything from how AI tools are changing the practice of design to how this impact the way we think about our career paths.

Some highlights:

Get 10% off Karl's Become a Design Engineer course: https://join.dive.club/karl

Today’s episode is with Karl Koch (https://x.com/_kejk?lang=en) and it’s filled with practical tips for new design engineers looking to push past what AI gives you out of the box.

We go deep into:

- Adopting the design engineering mindset

- What the job market looks like for design engineers

- The difference between frontend and design engineers

- Specific language to create better interaction design

- Th...

This episode is a deep dive into Rive—the engine powering experiences like Spotify Wrapped, next-gen car dashboards, and so much more.

After hearing Luigi and Guido Rosso’s vision for the future of interactive software, I’m convinced it will be a big deal for designers 👀

One of the biggest parts of my design practice is knowing which tool to reach for when coding with AI.

There are a lot of options and they’re changing every week 😅

So in this episode, I break down:

1. The mental model I use to think about different types of AI coding workflows

2. How that model guides which tools I actually reach for day to day

3. The new AI coding product I’m completely hooked on right now

- Tools listed:

- Lovable (https...

Sometimes you open up a website and it's so good that you're left wondering... how the heck did they pull that off?

In this episode the designer of the original Amie website, Xavier Jack (https://x.com/KMkota0), is going to give us a little tutorial of what it looks like to bring web experiences to life with 3D.

Some highlights:

- How he prototyped the viral Amie website

- How he made the Amie interactive balloons from scratch

- How he uses mental models to understand 3D design...

Last month the head of design at Lovable, Nad Chishtie, walked us through the portfolio of one of their recent design hires, Matt Sellers.

So today's episode is a behind-the-scenes of what it actually takes to create a portfolio that gets you hired at one of today's top startups.

He shares some really tactical mental models that I think everyone can benefit from.

Some highlights:

There's been a heck of a debate around the future of coding and design tools lately... but what's actually happening inside of today's top teams?

Where is all this headed and how does the future of our tools shape the role of a designer?

Today's episode is with Stephen Haney (https://x.com/sdothaney) who is the founder of the new design tool Paper.

And for the last few months he's studied how design teams actually use AI in their everyday roles... everything from tooling to prototyping to process.

He walks...

Gab and Nim are the co-founders of a startup called Dessn which allows designers to prototype in the context of their production codebase (without any of the setup).

So I asked them to hook it up to the Inflight repo and give me a little demo to see what’s possible.

I’m pretty sold 👀

Someone asked me recently... if you had to join a design team, who would you want to work for?

And my answer was easy... Perplexity

So today's episode with Henry Modisett (https://x.com/henrymodis) (Perplexity's VP of Design) is a deep dive into what makes their design culture so special.

Some highlights:

- How to create a culture of decisiveness

- What signals Henry is looking for in designers

- Factors that influence Henry’s leadership style

- How to lay the right foundation fo...

Kyle Zantos is leading the new UX Tools Labs where he's responsible for figuring out what matters for new design tools and workflows.

As a result, he's pretty quickly become my go-to source as I transition into more of a builder with AI.

So this conversation is a deep dive into very specific tactics you can use on your own design engineering journey.

We'll go through recommended tools, workflows, and Kyle's process for building a design engineering "Skill" using Claude Code.

We talk a lot about using AI at startups…

But what are more established companies doing to scale AI prototyping?

What are the best ways to use AI to prototype with your design system?

That's what today's episode is all about because we're talking with Lewis Healey (https://x.com/Lewishealey) and Kylor Hall (https://www.linkedin.com/in/kylorhall/) about how they scaled AI prototyping at Atlassian.

Some highlights 👇

- Their vision for a truly AI-native design system

- What's worked to scale AI prototyping adoption

...

Today's episode goes deep into all of the design details in a new video collaboration tool called Flask.

But the reason I’m so inspired by this product goes far beyond the UI/UX…

Flask is designed and built by one person—Enrico Tartarotti—who was a PM before this so his journey is the perfect example of what it looks like to thrive as a generalist builder.

So this episode tells the story of what it took to build a well-crafted product and all of the lessons that he learned along the way.

As one of the fastest growing companies in the world, Lovable is scaling their design team by tapping into the [Dive Talent Network](https://www.dive.club/talent-network).

So I interviewed their Head of Design, [Nad Chishtie](https://x.com/nadonomy), to learn everything I can about how to get hired as a designer at Lovable.

Some highlights:

- A breakdown of a recent design hire’s portfolio

- How to avoid getting your portfolio screened out

- How to crush the later stages of the hiring process

...

What does it look like to own web design for one of the fastest growing AI companies in the world?

And how do you get that opportunity if you don’t have companies like Apple or Airbnb on your resumé?

That’s what this episode with [Roman Tesliuk](https://x.com/RomaTesla) is all about.

He walks us through the Eleven Labs Figma and talks about the tiniest of design decisions all the way to how he’s building a scalable website system.

We also go deep into Roman's side projects and all...

I’ve probably learned more about visual design from MDS than anyone in the design community.

So I wanted to go deep into the creative process behind the all-new Shift Nudge website to see how he explores visual ideas.

He takes us through his Figma file that is full of very good ideas that didn't ship.

And he even shows us how he built his own Mosaic tool in v0 which became the core motif of the site.

So if you're interested in seeing the windy creative process behind one of th...

I get shown a lot of tool demos and one thing is clear…

Canvas-based UX will play a pivotal role in how we interface with AI.

It’s a big reason why Figma just bought Weavy 👀

So I interviewed Steve Ruiz who is the founder of tldraw where he's spent over 3 years and $5 million dollars building the perfect canvas (which powers many of the startups that we've studied on this show).

Some highlights:

In one of the most popular episodes yet, Vitaly Friedman talked about what’s next for AI design patterns (https://www.dive.club/deep-dives/vitaly-friedman).

In that episode he frequently referenced Shape of AIl (https://www.shapeof.ai/) which is an incredible database of AI design patterns.

So I wanted to get to the source and go deep with the creator Emily Campbell (https://www.linkedin.com/in/emmiecampbell/) to learn how to design great AI experiences. Because she’s studied AI products more than just about anyone I’ve ever seen 👀

Some of my fav...

AI is fundamentally shifting the way we think about digital products and the core deliverables that we're bringing to the table as designers.

So I asked Geoffrey Litt (https://x.com/geoffreylitt) (Design Engineer at Notion) to share his vision for the future of malleable software and AI system design.

Here’s some highlights:

- The keys to effective system design

- Geoffrey’s workflow for “working like a surgeon”

- Why too many products become “nightmare bicycles”

- The principles of malleable software vs. disposable software

- Why v...

Craft gets you hired.

But business impact gets you promoted.

So this week’s episode with [Ryan Scott](https://www.linkedin.com/in/ryanscottcreative/) is a deep dive into how designers can think strategically about their career.

He shares a ton of lessons from his [PM Masterclass for designers](https://join.dive.club/ryan-scott-pm-masterclass-affiliate):

- What it looks like to grow your product muscles

- The right (and wrong) ways to get buy-in for your ideas

- Strategies for making data a part of your design practice