Keenan Cummings: Product Design at AirBNB & Co-Founder of Wander


After years of working as a brand strategist and graphic designer I decided to move into product design. I cofounded a company in NYC called Wander, launched a product called Days, and later sold to Yahoo. I now lead the Experience Architecture design team at Airbnb. We build design systems to support the quality and consistency of product work at Airbnb and we develop new platforms for our users. On the side I run an event series called Designers Debate Club and blog at

What’s Your NativeAdVantage:

Someone described a T-Shaped creative as someone with “vertical expertise and lateral empathy”.

I have a few deep skills that set me apart: I work very fast, I can think and design in systems, and I can manipulate the gestalt of a logo or icon. (It’s the middle stuff that I tend to be clumsy and inexpert with.) These skills are where the “vertical expertise” comes from.

But I also feel that many designers have an inherent interest in all aspects of successful work. I am fascinated with the varied disciplines that are involved in making things. And even more so with the people and varied personalities. Engineers challenge my rationality; product managers challenge my diplomacy; writers challenge my clarity; etc. All of them challenge my humanity. This is where the lateral empathy comes from.

What do you do best?

Lead with energy and vision. I love the problem of getting a group aligned on a single big idea, and then keeping the energy level up so we can see the idea through.

What makes you the best?

I can never stick to something long enough to become great. I’ve had the privilege of being able to get just good enough at a lot of things. I’m lucky that I can make a career of that.

Never the best, occasionally great, usually good, always decent.

What are your aspirations?

Keep learning. Keep being challenged. Play to my curiosities not my strengths. Beyond that, I’d love to design a game.



“Success is measured by your willingness to have awkward conversations.” Also, “Never not stoked”.


I enjoy real people. I recently became fascinated by the idea of Normcore (not the misnomered, Larry David inspired fashion trend that was actually a concept originally called ‘Acting Basic’). From K-Hole, the coiner of the term and originators of the idea: “It’s the idea that an individual adapts to a situation at hand and embraces the normalcy of where they are and who they’re with.” To me this is what being real is. It’s more than being comfortable in your own skin, confident in your identity. It’s absolute comfort with changing who you are, adapting to your context, and sincerely, non-ironically enjoying anything that feeds mind and soul. It’s not putting on collegiate gear and ironically attending a game of “sportsball”. It’s the ability to jump between subcultures with it cynicism, fear, or irony, because those things and people are of genuine interest to you. It’s “fluidity of identity”, “empathy and connectivity.” To me that is what being real is.

And, above all, family. They are an extension of self and I am not whole without them.


From broad to specific: Anywhere in Korea; Stockholm, Sweden; Prospect Heights, Brooklyn; La Taqueria in SF’s Mission Neighborhood; a good chair with a stack of magazines; and, finally, in a state of creative flow.


Nexus 5 (so much more personality than iOS and more refined every day)


Eero Saarinen Womb Chair

Honda Ruckus

Topo Mountain Briefcase in Duck Camo

Diecast Enamel Pins by Diagonal Press


I like Video Games, Sci-fi, Debate, Children’s Toys, Identity, Youth Culture, Kanye West… it’s changing all the time.