Pay is below market for anyone even slightly senior.
Dogs running amok in the office were celebrated. (Maybe not a con for you, but there was no consideration for folks who didn't want to be interrupted by dogs going into or out of the conference rooms or begging for food or running around crazy because another dog came into the office. Every day.)
Many poor engineering decisions have left them several years behind where the industry is going. When I left there was no hint of any of Docker / Golang / Rust / Kotlin / Kubernetes / Nomad / etc. Frontend might be less stagnant.
The rallying cry of "We'll disrupt the commercial real estate industry!" gave way to becoming yet another data vendor making money off of huge landlords and not helping small landlords nor tenants. Too many *New York City* landlords can't afford the rather high prices CompStak wants to charge.
CTO is a macho bro man-baby, and really checked out except for when he shows up to crack the whip and intimidate people. We kept track and there was one month he only made it into the office six days, with a steady diet of oddball excuses for his whereabouts 15+ times. He should fully check out of tech.
CEO made jokes about confusing two Asian employees for each other, at a company wide meeting. He's quite fratty.
Leadership is quite passive aggressive and hypocritical. Before COVID, working from home was "allowed", but taking advantage of it more than once in a long while got you targeted and harassed.