Pros
- Generous hardware and software budget. - Competitive benefits. - Travel opportunities if you are into that. - A great place to have your first experiences as a remote worker. - A chance to work on open source projects (if you are assigned to them, or in your own time) - This is your place if you are a WordPress fan. But you could be disillusioned by looking behind the curtain.
Cons
- Some employees are more equal than others. Automattic used to have a lot of pride in its diversity and inclusion policies when hiring, but that has changed substantially in the last years when benefits and hiring shifted more and more towards US-based employees. Also, treatment varies a lot. US employees are treated with more leniency, whereas remote contractors are more... expendable. - There is absolutely no Engineering Practice You can choose your own tools, which is great. But there's absolutely no regard for who's coming next. There is no technical direction other than "open source is the best idea of our generation". Also, there are very poor and unhealthy metrics. - "Leadership" is incredibly inconsistent. Your happiness as an "automattician" depends greatly on how much overworked is your team lead. Because team leads are also required to not only manage people and projects, but also have regular output. Some leaders manage to concentrate on the first two, but even then, it depends on the projects. It's sad when leaders have to ignore the people side in favour of managing projects or writing code to meet a deadline. If that's your leader inclination, you can expect to have an awful time. - Communication is oxygen, except when it's not. No matter how openly and honestly you communicate, if your leader has too much pressure on the technical side, or is too inexperienced as a leader, brace yourself. You could easily be terminated if you have a bad time. But as I said before, there's more leniency towards US-based employees. - Projects are not finished, they are abandoned. There is no project management practice. Neither agile nor waterfall. Work is estimated based on which way the wind blows. Tracking of progress is non-existent and deadlines are set based on management "feeling" how difficult implementation is. That leads to deadlines not being met, priorities shifting and projects deployed to users with incomplete features. - Forget about having a career path. Automattic is a company that does not believe in titles. That in itself is not a bad idea. But a side effect of that is that as an automattician you have no goals for career development. You are encouraged to learn, but not provided with direction. So, in most cases, you'll pursue things that will either make your work easier or help you realize that your future is elsewhere.