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
• Gunnar’s journey learning metal shaders with Cursor
• How Gunnar strategically invests in his design skillset
• a lot more

• Perplexity - AI-powered search and discovery platform
• Cursor - AI-powered code editor
• Particle News app

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 future of HCI
• How Ryo handles a barrage of user feedback
• How Ryo approaches systems thinking at Cursor
• How Ryo unified the core primitives of Cursor’s system
• Laying the foundation for the future of Cursor’s system design
• Inside Ryo’s design process and how he knows what to pursue
• Why Ryo thinks specialization will matter less in an AI-enabled future
• Why Ryo believes the future of interfaces will match how people think
• a lot more

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 packaging.

Some highlights:

• Julian’s sources of inspiration
• Understanding Julian’s creative process
• The new analogy that Julian is working on for Linear
• Linear’s strategy for storytelling for their “Agents” release
• The importance of visual design in copywriting and marketing
• How Linear’s in-house creative studio collaborates on storytelling
• How Linear evolved from using “opinionated” to “purpose-built” over 3 years
• a lot more

• Antimetal website
• Arena for inspiration
• Julian’s website
• Linear’s hands of god visual for Agents release

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 systems in an AI-first world
• What Emmett looks for when hiring designers in the AI era
• Why liquid glass represents the wrong direction for design
• How Intercom’s AI product Fin overtook their core business
• Why the start of an S-curve is the best time to be a designer
• How AI is flipping the traditional product development process
• a lot more

• Plato’s cave analogy
• OpenAI’s forward deployed engineer role
• Apple’s liquid glass design
• Fons Mans helped on the design of Fin

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 Connor (VP of Design at Airbnb): https://www.dive.club/deep-dives/air-bnb

Alex Schleifer (former Chief Design Offer at Airbnb): https://www.dive.club/deep-dives/alex-schleifer

Janum Trivedi (prototyping specialist at Airbnb): https://www.dive.club/deep-dives/janum-trivedi

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 of “good” evolved from Arc to Dia
• Their process for exploring patterns for interacting with AI
• The #1 piece of advice Dustin would give younger designers
• a lot more

We mentioned Nate Parrott’s episode who was the first design hire at The Browser Company

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 from how their hype team operates
• How the design team has changed the way they collab with engineers
• a lot more

This is easily the most in-depth episode I’ve ever made so I hope you enjoy it :)

• Thomas and Petr (Raycast founders)
• Roy can Rooijen (Designing AI)
• Jordan Amblin (Designing mobile)
• Alexander Antonov (Designing windows + DS)
• Pedro Duarte (Hype lead)
• Inga Hampton (Designer + Illustrator)

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 on some of the things I'm learning, it turns into a video series that you want to keep watching ✈️

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 designers
• What designers can learn from the best communicators at Shopify
• Why Darrin believes designers need to think beyond static prototypes
• a lot more

• GKIII’s Cost of Craft article
• Frenzy drop sales product
• Astronaut video game that Darrin released
• Red Dot Design Award won by Shopify’s POS hardware

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 can use the code DIVECLUB to get your first month free 👌