Pros
Established remote work culture, genuinely some of the best people you'll ever work with, tech that is used by millions. Travel is a really cool perk, as is the three month sabbatical at five years. Used to be great, there's hope it could be again.
Kontras
Business is stagnating. Growth can feel limited due to tech stack. Salary is average, maybe slightly below average. Erratic leadership, especially the CEO, who was recently judged by an independent committee to have bullied and harassed WordPress community members. He also made a controversial situation on Tumblr worse via a public meltdown. The "Automattic" section of his Wikipedia page literally has more space occupied by controversy than business achievements. Internally, the term "Matt bombs" is common. He's known to be unjustly callous if he takes a personal dislike to someone and dishes out objectively bizarre, out-of-touch, damaging directives. Promotes and surrounds himself with sycophantic yes-men who enable his toxicity. There have been numerous poorly handled layoffs in which people in underrepresented groups were disproportionately affected. The environment is increasingly hostile to underrepresented groups. I've been privy to many misogynistic comments regarding women engineers. Leadership and HR are quick to dismiss valid feedback and avoid accountability. The company is declining as a direct result of poor decisions and direction from senior leadership. ICs are suffering the consequences of those poor decisions. Oh, and we were recently encouraged to leave positive Glassdoor reviews specifically in a bid to cancel out the impact of negative reviews. Again, feedback, no matter how valid, is simply swept under the rug and not taken seriously.