Vantaggi
Zillow was once one of the best companies I've ever worked for. The culture made you genuinely excited to come to work, you believed in what they were building, felt valued, and could see that leadership truly cared about its people. What Spencer Rascoff built was something special, a company with a true North Star. For a long stretch, it was exceptional.
Svantaggi
When a new VP of Sales was brought in, she dismantled the culture that made Zillow great. She stacked the organization with people she brought from her previous company, replacing proven leaders with loyalists who followed her in. I sat in meetings where leaders were explicitly told we needed to "skim the fat" and reduce headcount, starting with anyone who wasn't aligned with her vision. This wasn't restructuring. It was a targeted purge dressed up in business language.
Legacy leaders who stood up for their employees during this period were unceremoniously let go, not because they were wrong, but because they were fighting too hard for their people and not falling in line. These were the right leaders doing the right thing, and they were punished for it. If you want to understand the culture that was created, look no further than how reorganizations were communicated: employees who had given years to this company were let go while the VP delivered the news from a treadmill or eating lunch on a Zoom call. When the news went out via email, the departure of long-tenured employees was buried in the body of the message, a single line, sometimes not even mentioned at all. That is not leadership. That is indifference.
She let go of long-tenured leaders who helped shape the company, and quarterly employee surveys hit their lowest marks in over a decade. Rather than taking accountability, ironic for a company that lists "own it" as a core value, she blamed front-line managers. She lasted less than three years before being moved out, but the damage was done.
The mental toll on employees was real. People were taking mental health days and FMLA leave because the environment had become that toxic. When employees returned from using the very resources the company publicly promotes, they were penalized or quietly pushed out. Multiple employees raised the same concerns about returning from FMLA only to be placed on a PIP within 30 days, people who had never been on a performance plan in their entire careers. I experienced this firsthand, I had a mental breakdown due to the culture, was reprimanded within weeks of returning from FMLA, filed an HR complaint, and was told my allegations were unwarranted. Other employees who had raised the same concerns were never interviewed as part of my investigation. I was then told to return to work for the very person I had just reported.
HR is not your ally. Investigations are opaque, responses are scripted, meetings go nowhere, and retaliation follows. Compensation is equally frustrating, even top performers are capped at 3–5% raises, and stock options vest over four years in a structure that becomes a wash if you can't sustain peak ratings every single year.
What Spencer Rascoff spent years building was dismantled in less than five years. Zillow lost its North Star, the consumer, and shifted its focus to chasing revenue at the expense of everything that made it great. You can see it in the stock price, the survey scores, and the turnover. The unspoken message to legacy employees became clear: thanks for building this, but we don't need you anymore. I wanted to finish my career at Zillow. Instead, I was one of the people pushed out after giving everything to this company.
