Zillow’s first CDO looks ahead to a new era of ‘innovation and disruption’

March 1, 2022, 2:30 PM UTC

Jenny Arden talks about her career in design as straddling two very distinct sides of the same coin: left brain and right, business and design. Having grown up in Oregon as the child of a writer and physicist, Arden is simultaneously playful and pragmatic, both a dreamer and a keen-eyed strategist. “I thought I was going to be a painter,” she says. “…I kept evolving this career that had no path. If you had asked me when I was 18, would I be here as a chief design officer? I’d have no idea what you were talking about because it hadn’t been created yet.” A graduate of Rhode Island School of Design and Brown University, Arden started off in banking and has woven her way through posts at Airbnb, Lyft, Google, and Nike. In January, she started as Zillow’s first Chief Design Officer. Arden shares her thoughts with Fortune on design education, the power of design, and what most excites her about her new gig.

Fortune: When did you first realize you wanted to work in design?

Jenny Arden: I’m from Oregon. I had an affinity for the arts, and design and learned how to draw. I had internships and apprenticeships in the fine arts; I thought I was going to be a painter. I applied to RISD [Rhode Island School of Design] among other colleges and I got in, so I swooped over and got my first taste of the East Coast lifestyle.

What was your time at RISD like?

JA: I also realized early on, within the first year of being at RISD, that I had a deep need to be satiated on the academic side, so I decided I’d attend both RISD and Brown at the same time. I led this very interesting dual life. In the morning, I was a Brown kid taking classes and then I’d walk down the hill in the afternoon and take all of my studio classes. This shaped who I am: left brain and right brain needed to be satiated at the same time.

What sorts of lessons do you think a dual program like that offers the business world?

JA: The two schools are really different. One is more focused on academic rigor and one on the arts. That’s a series of skills you develop: problem solving, questioning the purpose of the problem and understanding multiple perspectives and sides of the story. These are all skills for any leader and certainly a design leader. It’s no longer that traditional path–there are so many other paths and you have to develop those skills. You need to have a multi-faceted way of looking at problems, especially as entrepreneurs. Coming out of moments of stress, you need to show your willingness to ride the waves and deal with failures and unknowns.

What did you think you’d do when you graduated?

JA: We were calling ourselves graphic designers at the time. What we were doing was deeply observing what people were trying to achieve, and then designing for that. We started to coin the terms interaction design and experience design. Product design came later.

Were you interested in business?

JA: I always brought one other flavor to this [career]: an obsession with the business side. I think there’s a creative component to that. There’s no way you could have defined a corporate job for yourself long-term. It’s been a wild ride and I would have never guessed it.

You started at JPMorgan and Goldman Sachs in banking… as a designer. What was that like?

JA: Every bank you can name, I have worked with. When you’re in that industry, no one understands design. So, you have to adapt and learn and become an industry expert very quickly. Your role was to shadow, and then deliver solutions that serve the people you’re talking to. There’s no opportunity to weigh pros and cons; it’s all about solutions.

Once I shifted into in-house consumer roles, Google and Airbnb, these were all organizations that had deep understanding on how to build technology. In banking, I am the outsider trying to advise what to do, versus I am one of the legs of this stool and this organization needs me.

You came up in a time in which there were quite a few unicorns launched and sent out into the business world. How did design play into the success of companies like Airbnb, Instagram, Warby Parker, SnapChat, and Uber?

JA: I often refer to 2010 to 2015 as a golden era, not just for design-led founders, but disruptive models. Everyone found themselves with the fundamental question of ‘is there a better way?’ Staying in someone’s home isn’t new, but normalizing staying with a stranger at scale was new. Hailing a car wasn’t new, but having them come to you and not paying cash was. It was also an interesting time for tech. During the financial crisis, many jobs weren’t available for smart [innovative] people. So, there was a little pressure, some smart people, and unique tech that all hit the market at the same time. The idea that, ‘I can do this differently, I have the tech to do it and I don’t have anything else to rest on.’ Ultimately grit, drive, and innovation created these user-centric platforms.

What can other entrepreneurs and Fortune 500 leaders learn from that?

JA: All of these companies were told their idea wasn’t viable. They were rejected for funding. What they were fundamentally doubting was behavior change. Would people let a stranger sleep in their bed while they were on vacation? A lot of people said no. What designers do–they have a strong vision that’s based off of a lot of research and intuition. For any Fortune 500 leader, data can take you so far. When you’re looking for actual change, there is a strong amount of intuition at play. You need to see the failures, pivot, and keep going.

It’s this idea that we need to solve a consumer centric problem and if we build something people love, they will come; versus trying to figure out how to make money and designing for that. It’s a different way of solving the problem. Now, though, we’re in the next chapter of highly matrixed organizations. It’s now just not a problem and a solution. Now we have 15 problems we are solving. It’s about using a common language across the company and helping people focus on what they can do really, really well. It’s way more horizontal. We’re now having to work together and figure this out together. Design leaders have a key role in that.

What is the problem you’re designing for at Zillow?

JA: People are discovering what might be their dream home but they can’t navigate without some pain on how to get that home. We are interested in solving the pain points along the way. One thing I learned [while working] at IDEO is that you look for extreme cases and you solve for that. And then, you solve for everything else. I love environments like this–the bizarre behavior. There are problems with the situation in the first place, and that’s why there are workarounds. It’s ripe for disruption.

There is so much happening because it’s an extreme market. There is behavior coming out of the woodwork, we have been in this unprecedented seller’s market. There’s a pretty risky assumption on the buyer’s side to get that home. I see this as an opportunity to achieve what people want–to win that offer. How can we help them? That means understanding what is motivating a seller to take an all-cash offer versus a traditional mortgage. And, how do you help in a way that both parties get that outcome they are looking for? The ‘How might we…’ statement we might present is, ‘How might we help our users win a bidding war with the most compelling offer?’ Then we break that down: What makes a compelling offer? We start with the actual problem, not the loophole.

How do you scale your design practice within the organization, while moving the needle for your user?

JA: I’m inheriting a very passionate team that was led by one of our co-founders. She led this team to understand the roots of Zillow, and they understand user behaviors and flows. The next chapter is about making sure everyone feels they are a part of the design process and can contribute. How do I use the language and the process for problem solving among my peer executives? They aren’t used to having these conversations or using ‘How might we…?’ statements. It’s about figuring out how we translate what users need and connect it to the business. Those are the correlations that need to happen.

How does your leadership style play into that?

JA: I’ve adopted a servant style of leadership. It’s a reverse pyramid. As a leader, you are here to celebrate and support the people doing the actual work. To earn the customer’s trust and guide people to a vision they can actually believe in. It took years for me to figure that out. I’m really proud to show people that another style can be done at the top. It’s an evolving area and ties to inclusion–not just women–but all of our backgrounds. I’m seeing more Black and brown women who are able to shine right now bringing unique traits to the business that weren’t there.

What most excites you about the CDO role?

JA: I love this space; I could talk about real estate all day. It spurs dreams. There are so many layers of friction and lack of education–especially for less affluent communities. There’s a lot of opportunity to help those individuals. I’m excited about combining Zillow’s deep understanding (we have the data) and use of innovation and disruption. This role is at the heart of the financial future of so many Americans.

How do you cultivate fellowship as a female design leader? What does that look like for you?

JA: For me personally, my community is not limited to design. They are my circle. I can say anything to them and they can say anything to me. Anytime you have a bad day you ping that chat it’s at your fingertips. Finding that crew is incredibly important for any female leader. For me, I haven’t found such a curated group just in design, but I have four or five colleagues who are working through the same things I am. We reach out to each other: we don’t just lean on each other but we are constantly pumping each other up so we know we are great. We have to repeat it to ourselves over and over. That’s a problem in leadership in general. You don’t get a lot of positive feedback. You hear when things aren’t going well. We need someone to tell us, ‘Actually, you are a great leader.’ You need to know to keep going.

Nicole Gull McElroy



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