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🤿 rainbow dogs

🤿 rainbow dogs

how to become an AI creative director

Ridd
March 02, 2026

How do you become an effective creative director with AI?

That’s what today’s episode with Jamey Gannon is all about.

There's clearly a moment in time right now where if you get comfortable with these tools you can really stand out in the market.

So Jamey gives us a behind-the-scenes of her process and it totally changed the way I think about the importance of prompting.

Some highlights:

What it takes to build a "daily taste practice"
Why direction is more important than prompting
Why consistency is the #1 marker of AI tool mastery
Sneak peek of her work for the new MagicPath brand
How she thinks about positioning herself in today's market
+ a lot more

🤝 WITH RAYCAST

AI is making it a lot easier to contribute to the Inflight codebase, so I’m knocking out polish tickets all the time.

And now AI agents inside of Raycast make that easier than ever.

Like let’s say I see something I want to fix…

In a single hotkey I can launch a Cursor background agent, add a screenshot or any context that’s needed, and then manage the entire process directly inside of Raycast ✨

You can ship code as quickly as it would take you to type up a new issue in Linear.

It’s a big deal for designers and you can start using it today 👇

🔑 KEY TAKEAWAYS

AI Creative Director

1 — Consistency is the real skill marker

It’s not hard to create something beautiful with AI. The true sign of mastery is consistent, repeatable results.

2 — Direction > Prompting

I’m pretty convinced “prompt engineering” won’t matter in the long run. And honestly it’s relieving.

Jamey puts way more emphasis on strong creative direction (reference photos, mood boards, etc.). She showed me her setup for MagicPath’s new brand and she’s at the point where she can simply prompt “dog” and get something really unique.

“Stop prompting and start using reference photos”

Jamey Gannon

3 — Work in tiny, surgical steps

She uses Flora to set up image-gen pipelines where she’s editing a single variable at a time. For instance she’ll grab a specific pair of shoes she wants her model to wear from Google images and then feed that into Flora.

4 — Daily taste practice

The reason I found this conversation encouraging was it really wasn’t about the tools… Jamey is seeing success as a brand designer with AI because she has impeccable taste and at the end of the day that’s all that really matters 🤷‍♂️

Taste comes through reps. Jamey showed me her Pinterest setup and she has over 15,000 pins 😮

5 — Window of opportunity

There’s real alpha in calling yourself an “AI designer” right now. Jamey thinks there’s only ~100 people doing it.

But eventually this will be the same as saying “Figma designer” or “Food chef”.

If you want to go even deeper:

I asked Jamey to share a discount code that Dive Club listeners can use for AI Creative Director
The full episode is available on Youtube

👥 FEATURED RESOURCE

How to get hired at today’s top startups

Whenever companies I like start hiring, they usually ping me to see if I know anyone great…

So I put together a list of the most talented designers and builders to recommend to my favorite companies (including some seriously cool stealth startups).

You only talk with companies you want to meet and the whole thing is designed to be an easy way for talented designers to see what’s out there without having to be public about it.

So if you’re open to new opportunities, take a second to claim a spot in the new talent network 💪