Adrian Phillips didn’t set out to become a design leader.
He was on track to study law.
Then became a software engineer.
Then… joined a touring musical group called The Ten Tenors and performed around the world.
Today, he’s the Head of Product Design at Yahoo, and has led teams at Airbnb, Lyft, and Asana.
In our latest episode, Adrian shares his fascinating path—and the deeply practical lessons he’s picked up along the way.
In this conversation, we cover:
• The unlikely connection between performing arts and product design
• What it takes to scale culture in a 100+ person remote design team
• How to balance speed vs. quality in high-growth environments
• Why leadership isn’t about titles—but about storytelling and influence
• How AI is already reshaping design workflows
• The #1 trait he looks for when hiring designers
This episode is packed with insights for anyone building or leading design teams—especially those navigating org growth, remote work, or the AI shift.
🎧 Watch now:
• YouTube
• OpenDesignDocs.com
3 Takeaways I Loved:
You don’t need a title to lead.
Leadership comes from craft, storytelling, and the willingness to share what you know.Quality is a team sport.
The best teams don’t say “I’m blocked by design”—they build shared ownership across design, PM, and engineering.Rituals scale culture.
Crits, mentorship, async huddles, and occasional in-person meetups are the glue of a remote-first org.
Thanks again to Adrian for being so open and generous in this conversation.
If you’re early in your career—or managing designers at scale—I think you’ll get a ton from this one.
Hit reply and let me know what resonated with you.
– Jason Culbertson
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