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:

• Redesigning the Shopify checkout
• Ron’s unique research tactics for UberEats
• Building MTCHMKR from scratch in Lovable
• Navigating the job market as a design leader
• a lot more

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:

1. Meaghan Choi who is the design lead for Claude Code and Cowork
2. Dan Shipper who is the CEO of Every and one of my favorite thinkers when it comes to AI
3. And Bradley Ziffer who is a design engineer at Ramp

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

The event was hosted by Double Diamond and Ramp

⭐️ 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 highlights:

• Building one of Notion’s most visible UIs
• Why recreating interactions teaches you craft
• Owning the last 5-20% of frontend polish work
• The “jelly bean factory” problem with AI output
• When to start in Figma vs. jumping straight to code
• How Andy creates prototypes that content teams can edit

• a lot more

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:

• Why 59% of designers build their own tools
• Tommy’s current tool stack for AI design work
• What signals show AI fluency in job interviews
• Why internal tool building is the new career path
• Why now is the best time to grow in the design community
• How design workflows have become creative director roles

• a lot more

Ben Blumenrose (mentioned as having good insights on design)

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:

• Balancing metrics and vision
• Redesigning the shopping cart UX
• Taking a big bet on the shopping feed
• How product strategy has changed with AI
• How to get people excited about your ideas
• How to make sure you don't overcook your app
• a lot more

• Katarina mentioned John Rundle and Luke Dupont

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

- Balancing accessibility and delightful UX

- Behind the scenes of Rafa's side projects

- + a lot more

- Metal Gear Solid (PlayStation 1) — directed by Hideo Kojima, referenced for its fourth-wall-breaking design moments (Meryl’s codec frequency hidden on the game box; Psycho Mantis boss fight requiring the controller to be switched from port 1 to port 2)

- Sunlit app — gyroscope-based app for tracking sun position and light direction, referenced as a recent example of surprising UI: https://play.google.com/store/apps/details?id=io.lonepalm.coloringworld&pli=1

- Retro app — private social network for friends and family (what Instagram used to be); Rafa’s current employer: https://apps.apple.com/us/app/retro-photos-with-friends/id6443709020

- Splat app — Retro’s generative AI app for iPad/iPhone that turns photos of kids into coloring book pages: https://apps.apple.com/us/app/splat-magic-coloring-book/id6749165093

- Hand Mirror app — Rafa’s most popular side project, a menu bar camera app: [https://handmirror.app](https://handmirror.app/)

- Gabe Valdivia’s episode — early Dive Club episode (~ep. 30) where Gabe talked about designers needing to be like “little TikTok creators” inside their orgs: https://www.dive.club/deep-dives/gabe-valdivia

- Final Cut Pro — Rafa’s video editing tool of choice: https://creatorstudio.apple.com/info/try?itscg=20201&itsct=acs-sem-187498456050-794866723417&pt=2003&ct=css-187498456050-794866723417

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 WealthSimple

- Polly’s go-to interview question to evaluate designers

- How AI is changing team composition and design roles

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 it takes to thrive while designing a 0→1 experience

- How Brandon is positioning himself as a new independent

- The difference between "seeing taste" and "creating taste"

- What Nikita (X Head of Product) taught Brandon about onboarding

- + a lot more

- John Lasseter (Pixar director) quote - https://www.youtube.com/watch?v=uFbOOjAC_Fg

- Tolan app (mentioned as example of creative onboarding) - https://www.tolans.com/

- Owen Jennings at Block (Brandon’s mentor for 4 years) - https://www.linkedin.com/in/owenbrittonjennings/

- Nikita (former Head of Product at X) - https://x.com/nikitabier

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 wrangling AI then you’re going to love this episode.

Some highlights:

- Why his first Notion design offsite was so impactful

- How Brian built Notion’s prototyping playground

- Why Brian has started using Cursor again

- Practical tips for prompting AI more effectively

- Behind-the-scenes of Brian’s new side project

- How to stay relevant as a designer in an AI world

- + a lot more

- Agentation and Dialkit for frontend ([https://agentation.com](https://agentation.com/), https://joshpuckett.me/dialkit)

- Cursor and Conductor for coding ([https://conductor.build](https://conductor.build/))

- Brian’s side project Shiori ([https://shiori.sh](https://shiori.sh/))

- Max Schoening nerd snipes Brian (https://x.com/mschoening)

- Karri’s issue tracking is dead article (https://linear.app/next)

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:

****

- 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 makes designing with AI as a material so unique

- How tools like Codex are changing the practice of design

- + a lot more

- Mike Matas and Brandon Walkin (creators of Origami) https://mikematas.com/ , https://medium.com/designatmeta/introducing-origami-live-and-origami-2-0-a68116294e65

- Cursor and Codex (AI coding tools) https://cursor.com/ ,(https://chatgpt.com/codex/?c_id=23226110534&c_agid=188421385415&c_crid=800871103650&c_kwid=kwd-111182835&c_ims=&c_pms=9017288&c_nw=g&c_dvc=c&gad_campaignid=23226110534&gbraid=0AAAAA-I0E5dO-SVXduV4xJjtnqTNMNrAP)