Pros: Great remote culture and benefits.

Cons: Pay was meh for a (mostly) American company. WordPress has a stinky codebase. Things went crazy with the whole WP Engine debacle. Joined at the worst possible moment.

Pros: + Benefits + Compensation + Time off / Flexibility

Cons: Pretty flat company, so the opportunity to "move up" is limited for those looking to get titles under their belt while company hopping. Personally, this is a positive, but I know it bothers some.

Pros: Even after 10 years, I'm shocked to discover that I still really enjoy going to work every day. The work is interesting, the bureaucracy is mostly kept to a minimum, and – most importantly to me – the people really care. They care about each other, our customers, and about the effects of our work on the world. I love that we have a creed and actually try to follow it. I communicate more often and more skillfully with my co-workers at this remote job than I ever did working in an office, and this has made all the difference.

Cons: As products are developed, there is always technical debt created. If developers do not continue to refine their products, this debt accumulates, causing problems for customers and product teams alike. Automattic's teams have a long history of shipping a v1 and then being reassigned to the next big thing, leaving unowned features throughout. There's been some work to correct this cultural deficit, but I think there's still more to be done.