Pros
There's a wide range of interesting products, projects, and problems to work on. You'll never be bored. The people are kind, everyone is smart, talented. It's a full distributed company with many opportunities to travel and meet others.
Cons
For having existed for nearly two decades, Automattic is extremely organizationally immature. You might expect to join and think that it would be a well working oiled machine. Think again. Every company has it's issues, right? No place is perfect. That's what I told myself at first to dismiss my early concerns 3 months in. Time has passed, I see it for what it is now. Automattic behaves and acts as if it's a scrappy small startup but it has nearly 2000 employees. Things you might take for granted at other companies are painfully broken or missing entirely at Automattic. There are no broader company goals. There are no clearly defined roles, levels, or pathways for career growth. Annual reviews? That's called a google doc and however your lead decides to format and write it. Roles have no clearly defined and communicated proficiencies for which your performance is judged on. So everyone ends up being judged on whatever your lead thinks you should be doing better, which is often vague, unclear, and difficult to measure. Feedback? That's a surprise waiting for you at your mid year and annual reviews. Do not expect timely feedback. Working at this company has actually made me appreciate how competent HR was in past roles. I see now what flaws a company can have when HR's solution to everything is "talk to your lead". There is zero accountability or communicated expectations for leaders here. There is no required management training. There is no psychological safety. People are often fired after being given feedback they've seen for the first time. You will find most people here are disengaged and checked out. Why? Because they do not listen to feedback. It's not hard to see why when Matt Mullenweg berates people on slack. It's one thing to give a team feedback, it's another to use your CEO role to treat them in a disrespectful and demeaning ways. There is no trust or confidence in his leadership. This company has been coasting on it's success since the early 2000s and it's honestly impressive that they've managed to stay afloat for so long. If you are a future candidate, looking at potential roles. Please trust me when I say you should avoid this place, do yourself a favor and do not entertain roles or offers from Automattic. By the way, they openly solicit people to post positive reviews to counter the negative ones. So any positive reviews should be read with that context in mind. That's not to say that there aren't happy people here who love it. There indeed are some people who are happy here, who are passionate, and plan to work here forever. But they exist in a small bubble. Maybe a small team that does things the right way, and they're shielded from a lot of the day-to-day BS.