Inman Connect Las Vegas returns live, Oct. 26-28, 2021, at the Aria Hotel and Resort in Las Vegas, Nevada. In the lead-up to the big event, we’re talking with scheduled speakers about the moments that made their careers. Consider this just a taste of all the knowledge that will be shared at ICLV. Make plans to join us.

Zillow President Susan Daimler just stepped into her role last February. But the promotion — she had previously been a senior vice president at Zillow — was the result of a long a circuitous path.

Daimler began her career in marketing more than two decades ago, then went on to found multiple companies. By 2012, she had joined Zillow to oversee New York City operations as a senior vice president. And in total, she’s been at the portal for nearly a decade now.

For much of her career, Daimler has also been one half of a power duo with her husband Matt Daimler. The couple founded two startups together, and eventually joined Zillow as a pair. Matt is also still with Zillow — he’s a senior vice president — and the couple’s relationship highlights a rare but effective approach to balancing personal and professional life.

Susan Daimler will appear at Inman Connect Las Vegas next month, and in the lead up to that event, recently sat down with Inman to talk about key moments in the journey to where she is today.

Founding startups

Daimler founded her first startup in the early 2000s.

She told Inman that at the time she and her husband were traveling frequently for their jobs in marketing and tech, respectively, and would typically fly coach. But often on those flights, the Daimlers would notice that they weren’t sitting in the best spot on the plane.

“It came from personally doing very long legs of travel for work,” she said, “and seeing people in flights with better seats.”

From those countless hours in bad airplane chairs, SeatGuru was born. The company launched in 2001, and gave travelers color-coded maps of airplane seats so they could make informed decisions about where to sit. By 2007, travel giant Expedia had bought the company.

Daimler said that she and her husband were living in Seattle at the time, but decided to move to New York City. That experience led to their second startup: Buyfolio.

“We bought an apartment in New York City and really struggled with the coordination,” Daimler recalled. “It was so hard to keep the conversation going. So we started Buyfolio as a [software as a service] to help agents coordinate with their homebuyers.”

Buyfolio launched in 2009 and several yeas later sold to Zillow, which kept both Daimlers on in executive roles.

Though Susan Daimler’s two startups were founded years apart, she said that, on reflection, both taught her a similar truth about “having a real focus and empathy for an end customer, relentlessly and intentionally so.”

“I think a lot of people start companies and they think about solving big problems that they haven’t experienced but that they think will result in success,” she continued. “But in order to really understand the customer, you have to really understand the problem, and have lived it yourself.”

Daimler described this concept as “entrepreneurial empathy” and said it has continued to inform her life and career in the years since.

Leading authentically

As the founder of a pair of startups, Daimler was typically leading small teams. She described both SeatGuru and Buyfolio as herself, her husband and a handful of developers.

But as her career progressed and she assumed leadership roles at the comparatively massive Zillow, Daimler increasingly found herself leading larger groups. In some cases, she was overseeing meetings with thousands of people. In other cases, she was the only woman in the room. And over time, that environment created pressure.

“There were a couple of moments over the years where I saw that perhaps I had strayed a bit from my authentic self and my best self,” she recalled. “Sometimes you’re sitting there and you are becoming what you think the room needs you to be verses who you are.”

But about six years ago, Daimler started trying to correct that. A big part of that transition involved reflecting on how to be a better leader, especially as a woman in a business environment where men still hold most top positions. It also had to do with having kids, which forced Daimler to think even more deeply about the balance of her professional and personal life. It wasn’t a single instant, in other words, but a slow burning epiphany: She wanted to be more authentic.

“It certainly has changed how I lead, how I show up,” she said.

In practice, this shift has meant Daimler had to get comfortable with being more vulnerable. She became more open about her personal life, and more frank about her many different roles, both in and outside the workplace.

“It’s opening a 7,000 person meeting and being willing to say things are tough right now,” she explained. “It’s saying, ‘I won’t take that call, it’s bed time at my house.'”

People are everything

Daimler first met her husband in college in the 1990s. Soon after graduating, the couple packed up a car and moved across the country to California’s Bay Area, and it wasn’t long until they had begun work together on their first startup. From that first moment would come a life-long personal and professional partnership, and the second slow-burning realization Daimler shared with Inman: The people you work with can make or break an experience.

“What’s better than every single day working most closely with the person you trust the most?” Daimler asked. “Someone who cares as much about you as they do about themselves? When you see what can come from that you want to be around that all the time. Being with your spouse, you can be your true self.”

She went on to explain that she was “spoiled early on” due to her positive working relationship with her husband. And while of course not every professional relationship can look like a marriage, the experience has taught her that its essential to surround herself with supportive people.

“It’s a recognition that the people around you are everything,” she said.

Daimler noted this has translated into how she builds teams, and how she looks for colleagues who “challenge each other and can get after it together.” And she ultimately concluded that the process of learning this lesson “has been a journey.”

“The ‘aha’ moments come from a whole bunch of reflecting,” she added. “And then it’s, how do you take what you’ve learned and turn it into something good?”

Email Jim Dalrymple II

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