Pros
When I joined, Zillow really was one of the Best Places to Work. I liked my managers, co-workers, and the many fun Zillow traditions. I thought that Zillow did a good job providing good perks and useful benefits while avoiding a lot of frivolous nonsense. When they went all-remote in 2020, the company really did do as good a job as could be hoped for managing that transition and being supportive of people's physical and mental needs.
Cons
I think it was very clear to anyone who interacted with, like, real customers that Zillow Offers was a terrible program from the start, that antagonized and annoyed users, and had very little potential. It was pure glistening hubris in the C-suite that pretended it was otherwise. But worse was the creeping stagnation that consumed the whole rest of the company. So many multi-year "platform rewrites", hair-splitting A/B tests and an absolutely pervasive sense that no one knew what they should do or how to get it done. The "old" businesses of rentals and forsale listings just chugged along doing *nothing* for years, honestly YEARS. Look at zillow.com from two years ago, there's been no real improvements. People were obsessed with Redfin, but it was like they were looking through a window at a puppy they could never hope to snuggle. A lot of senior managers and leaders are still around from the old easy money days, and there's a common feeling they're just protecting their turf and not wanting to rock the boat. These guys (and all are guys, to be clear) shuffle a lot of middle managers around, debate the meaning of words in OKRs, all the usual corporate theatrics. But so little was actually accomplished, so so little. It's just a regular big dumb company now I guess.