The Best Career Advice You’ll Ever Get

Zillow COO and General Counsel Kathleen Philips shares three words that got her where she is today: “Just try it.”

By J.R. Ball

“Two roads diverged in a yellow wood, and sorry I could not travel both, and be one traveler, long I stood, and looked down one as far as I could… I took the one less traveled by, and that has made all the difference.”

If one can forgive the clichéd use of Robert Frost’s oft-cited poem “The Road Not Taken,” its four stanzas of iambic tetrameter perfectly encapsulate the trepidation found in many of life’s most momentous decisions. While Frost may have had regret in mind when penning the piece, for some the fork in the road need not be a source of self-doubt and critique. Rather, it may be the first step down a path to a life that otherwise could not have been imagined.

For Kathleen Philips, Chief Operating Officer (COO) and General Counsel for the online real estate marketplace Zillow, the fork in the road was met nearly two decades ago. After leaving the Bay Area to accompany her future husband to Washington, D.C., Philips put her career as a paralegal on hold indefinitely. As life would have it, her professional pause would be short-lived.

“I thought I would never go back to work,” Philips said. “After a little more than a year, it became clear that I wasn’t the sort of person who couldn’t not go to work, so I took the LSAT and applied to law school, but I really wasn’t sure if that’s what I wanted to do.”

The alternate path Philips considered had more to do with luggage and layovers than law.

“At the time, I also seriously considered becoming a travel agent,” she said, admitting that her decision ultimately boiled down to one decisive moment. “I kid you not, that’s how it happened. I never had any specific path for the law in mind. I just thought, ‘If I’m going to have a profession, this might be a good one.’”

For Philips, law has been a good profession indeed. As General Counsel for some of the Web’s heftiest startups, including Hotwire and Stubhub, she has not had much time to regret or second-guess her decision. In fact, Philips puts a fine point on not looking back.

“I’m pretty sure you wouldn’t be interviewing me right now if I were a travel agent,” she noted.

A Solid Foundation

A University of Chicago law graduate who entered private practice early in her career, Philips’ decision to forgo life as a travel concierge in lieu of legal studies would one day come full circle—and would also serve as a stepping stone for her eventual journey to Zillow.

In 2000, while an Associate with Palo-Alto based Cooley Godward LLP, Philips was approached by Hotwire Chief Executive Officer (CEO) Karl Peterson, a Cooley Godward client, to become the online travel site’s General Counsel. Her reaction was initially met with skepticism.

Peterson’s advice to Philips was to “just try it.” “So I did,” she said. “And I haven’t looked back.”“I said that might it be odd for me to serve as their General Counsel,” Philips said, “considering that I was not a corporate lawyer and I didn’t know much about corporate law.”

At Hotwire, not only would Philips cut her teeth in the world of corporate law, but she also would lay the groundwork for lasting relationships with many of the same key executives who, in 2005, would form Zillow in Seattle.

“We grew Hotwire into a significant business, and we were later acquired by Expedia,” said Philips, who notes that Zillow CEO Spencer Rascof was a Hotwire Co-Founder and Vice President, and that Amy Bohutinsky, Zillow’s Chief Marketing Officer, was Head of Communications at Hotwire. And several Zillow executives, including Chairman Rich Barton and Vice Chairman Lloyd Frink, are Expedia alums.

The advantages of having an established history that stretches back nearly 15 years is, in Philips’ words, ‘terrific.’ “We have a deep and engrained history, which is terrific because it shorthands many discussions,” she said, acknowledging being the “newbie” amongst her former cohorts, having joined Zillow three and a half years ago.

“We know each other so well,” Philips said, “and we share common values. We’re all on the same page, and it makes it much easier to get our work done.”

Home Improvements

During Philips’ tenure as General Counsel at Zillow, the brand has experienced tremendous growth, having undergone several recent acquisitions—including those of HotPads, Mortech, RentJuice, AgentFolio and StreetEasy—not to mention the launch of five additional sub-brands under the corporate umbrella. The inherent challenge, according to Philips, is making sure Zillow’s house is in order to welcome and support new companies entering into the fold.

“As we go out and acquire companies that we think are fantastic, all of which have uniquecultures, we want to make sure we’re preserving their best features,” Philips said. Creating consistency across the entire Zillow organization, she added, is a top priority.

“It’s a balance between providing resources for the acquired companies to grow and develop, but also making sure that we have a unified set of values across the entire organization.”

The key to sustaining a healthy growth trajectory while ensuring Zillow’s corporate culture is as hungry and vibrant as the day the business was launched, per Philips, is to never stop behaving as a startup.

“As an organization grows,” Philips said, “it becomes harder to maintain that culture. You see that businesses our age often start to slow down and become a bit stodgy. We’re
hyper-focused on making sure that doesn’t happen. That’s why we hold on to our startup spirit.”

Strong Structural Support

As COO, much of Philips’ workload is consumed by responsibilities beyond the General Counsel role, including oversight of customer support, corporate development for mergers and acquisitions transactions and human resources. But the latter title remains her foundation within the organization, as are the lawyers on her team.

“At the time Zillow went public in July 2011, the Legal Department was comprised of just two lawyers,” Philips said. “While we’ve grown, my favorite thing to say about us is we can still ride around in one car.”

Philips is keen to bring lawyers to the table who not only seem to be a good fit culturally, but also offer a high degree of specialization in order to meet the needs of a rapidly growing, publicly traded company.

“It became clear after the IPO that we needed some securities expertise on our team, and it just so happened that the lead associate on our outside IPO team was looking to make a move,” Philips said. “About six months later, we added a Senior Corporate Paralegal who is instrumental in SEC compliance efforts and is able to take on work far beyond the scope of a Paralegal. And most recently, in January of this year, we added another Corporate Counsel for Securities.”

Philips’ top-down approach to guiding her legal team mirrors the overall mission of Zillow: to be innately focused on customer service.

“Our orientation is very clear,” she said. “Our Legal Department is focused on client service, and in order to support the organization, we look for people who understand that the job of an in-house lawyer is to facilitate business as well as to provide excellent service to our clients.”

Due in large part to her effective management of the legal team, Philips was able to make a soft transition into the COO role in August 2013—duties she already had been executing.

“I’m supported by such incredible people,” Philips praised. “I am able to work in a variety of disciplines at Zillow because of my awesome legal team and their support and understanding.”

From her humility to her genuine appreciation for her peers and associates, there is not much more you could ask of a COO and General Counsel. Other than perhaps that she book your vacation travel accommodations. But fortunately for Philips and Zillow, we all missed the boat on that one.

J.R. Ball is a freelance writer based in Dallas, Texas.