Dive Club 🤿

Last month we did the ultimate Raycast Deep Dive , but there's a lot in there… so this week I want to highlight just the segment from the product design team. We go deep into how they collaborate, why they’ve started shipping more code, and what it takes to build a culture obsessed with craft. Don’t forget to use code DIVE20YT to get 20% off your first purchase of any Lovable plan ❤️ Valid until A...

This week, Gunnar Gray (Product Design Lead at Perplexity) dives into the art of designing AI-native experiences. He shares lessons from shaping Voice Mode and how prototyping with AI is changing the design process at Perplexity. Some highlights: Why Perplexity is racing to get ideas into code What it’s like designing at a hyper growth startup What it’s like designing dynamic voice experiences Gun...

Cursor is easily one of the most impactful companies in all of tech… And this week's episode is with their Head of Design, Ryo Lu. You might've heard of Ryo in this episode back when we talked about early Notion and systems design. So this week we're going to get an inside look at how design operates at Cursor and all of Ryo's experiments with AI 👀 Some highlights: What Ryo believes about the fut...

This week's episode is with Julian Lehr who is the storytelling lead at Linear So we're going to step out of the pixels for this conversation and focus more on how you can get people excited about what you're designing. Because in the age of AI, stories are what makes your product defensible. So we're going to go deep into Julian's creative process and how he kinda thinks of his role more as packa...

You probably know Intercom… but did you know they recently incubated a new startup called Fin that has already surpassed the core business? They’ve pulled off a massive transition to an AI-native product and design org so today we’re going behind-the-scenes with their VP of Design Emmet Connolly . Some highlights: Why Emmett believes designers will own the frontend The opportunity for design syste...

In last week’s episode , the Head of Design at The Browser Company shared a totally new way to think about your portfolio. He says one of the most valuable things you can demonstrate today is the ability to solve real problems with code (no matter how small). I’m literally doing this with a side project right now and I’ve learned a lot so I decided to share my new playbook for vibe coding 👇 Teo C...

Dia from The Browser Company has completely taken over the internet. We’re finally seeing what an AI-native browser can be and it’s pretty exciting :) So this episode is a behind-the-scenes with their Head of Design, Dustin Senos . Some highlights: How to build a product strategy around AI How The Browser Co approaches prototyping Dustin’s perspective on MCP and agentic design How their definition...

This week’s episode is a first of its kind because we’re doing the ultimate deep dive into one of my favorite products: Raycast We’ll here from the founders, design team, and even the hype team and go deep into all kinds of topics: The hilarious story of Raycast’s YC application 3 weekly rituals that are perfect for remote teams What they’ve learned about designing AI experiences What we can learn...

The last two weeks with Inflight have been the most exhilarating of my entire career… So I want to use Dive Club  to provide unprecedented levels of access to life as a design founder. I’m talking about the messy behind-the-scenes, hideous Figma concepts, and all of the winding turns that we've taken to get where we're at today. This is gonna be as raw as it gets. And hopefully by shining a light...

This week's episode is with Darrin Henein who is the VP of Design at Shopify. We talk about how they create a culture of excellence and how AI is influencing the way they practice the design. Some highlights: What makes for a great design critique culture Darrin’s expectation for how designers prototype How Shopify’s new AI mandate impacts designers Traits Darrin notices in promising younger desig...

There’s a new design tool called Subframe that’s officially caught my eye 👀 So I asked their co-founder Filip Skrzesinksi to give us a demo and talk through their vision. I found some of their AI interaction patterns fascinating (especially the way they approach prototyping and contextual edits). If you’re interested in the future of design tooling then I think you’ll like this episode and you ca...

There are two types of companies today: Startups birthed out of AI Existing companies figuring out how to adapt to AI This week’s episode is all about #2 because we get to hear from Ioana Teleanu who was the first AI designer at Miro and is now a dedicated AI+Design consultant. So a big theme of this conversation is how to identify the right opportunities to design AI into a product that’s already...

This week we get to hear from Jesse Kulp who is the original designer for Google AI Studio. He shares what it was like going 0→1 as the sole designer and his ideas for where AI design is headed next I think we're gonna look back in a couple years, the kind of silly stuff we're doing today and say it looks like child's play… Jesse Kulp some highlights: How Jesse transformed into the ultimate genera...

Stephen previously co-founded Modulz which created Radix UI, now used by Vercel, Linear, and Jetsi. Now he’s the founder of the most influential design tool on the market — Paper . In this episode, Stephen gives us a look at how Paper is fundamentally changing the speed of traditional design flows. Some highlights: How to drive alignment as a company How Stephen cultivates empathy in designers How...

A year ago, it felt like AI-generated UI was about to have its moment. But now the landscape looks a LOT different than what people expected. So this episode answers the question "what's next?" Because there's still an untapped opportunity that I believe will become very real soon... Kyle Turman (Designer at Anthropic) https://www.dive.club/deep-dives/kyle-turman Nad Chishtie (1st designer at Lova...

This week, Zach Leach (Head of Design at Gamma ) gives a behind-the-scenes of what it’s like designing one of the hottest AI products in the world today. He shares a ton of techniques and lessons learned from working with LLMs—including some ways to make AI fun again :) And we also learn what makes design at Gamma a bit unorthodox in all the best ways. Some highlights: What makes Gamma a team of “...

The more I study today's top design teams, the more clear it’s becoming that we're entering the era of a new type of design leader— one with taste and the skills necessary to uphold craft. So this episode studies this new archetype of leader by highlighting clips from design leaders at Airbnb, Ramp, Duolingo, and more… Alex Schleifer (Former Chief Design Officer at Airbnb) Mig Reyes (VP of Product...

Mig Reyes is the VP of Product Experience at Duolingo (and a design director at Instagram before that). In this episode he shared a behind-the-scenes of how design operates at Duolingo (as well as some harsh truths designers need to hear). Common portfolio review mistakes How communication skills build influence Mig’s strategy behind hiring junior designers How to succeed in executive product revi...

I talk to a lot of designers at the pinnacle of their career… So I’m always trying to figure out how they’ve evolved the way they practice design over the years. Once I hear the same answer from a few different people I start to pay attention 👀 So here are a few trends I’m noticing for how the best designers get alignment on their teams. Alex Cornell (Gen AI at Meta) Yuan Wang (Head of Design at...

Anthropic has quickly become a category-defining company and in this episode Kyle Turman (their first full-time designer) shares a behind-the-scenes of what it was like designing Claude. If you’re interested in startups, AI products, or the art of prompting then this conversation will be right up your alley. Some highlights: Kyle’s story of wearing every hat for Claude What it’s like designing con...

There's a parallel I'm noticing between what's happening today with AI and what happened way back in 2013. So this episode studies the early days of Snapchat, the emergence of high-fidelity prototyping tools, and answers the question “what does it look like to have agency in 2025?” Jack Brody (Chief Product Officer at Suno) Jorn van Dijk (CEO of Framer) Julius Tarng (Research engineer at Anthropic...

Tuhin Kumar has designed at some of the most prolific companies in the world (early Facebook, Airbnb and Apple). But everything’s changing in his new role… Because now he’s the Head of Design at Luma AI which is one of the companies leading the charge on generative AI. So this episode goes deep on how the value prop of design is shifting. Some highlights: The #1 trait of craft-oriented companies W...

There are two goals that designers almost always group together: Make a useful product Make it easy to understand But my interview with Sam Stephenson changed my thinking completely 👀 So this episode breaks down Granola ’s go-to-market strategy and why I’m copying it for my own startup. Sam Stephenson (Co-founder of Granola) Colin Dunn (Co-founder of Visual Electric)

Jack Brody joined Snapchat as one of the early designers where he spent 10 years and eventually became Head of Product. So this week’s episode features a lot of lessons learned from the early design team at Snap and an inside look at what makes their culture so special. But we also go deep into Jack’s new role as the Chief Product Officer at Suno where he’s helping design the future of music. So w...

I’ve interviewed a lot of designers who have landed some pretty high profile roles and I’m starting to notice some trends 👀 So this video breaks down 6 portfolio tips that you can use to stand out.