Pros: A great place to work for working schedule flexibility, global remote and asynchronous communication culture. Excellent salary opportunities for developing world countries. Unlimited PTO, great parental and sabbatical leave perks.

Cons: - Faces growth issues that leadership seems unable to deal with. - No product development culture. It relies on volunteers to lead without the required skills or credentials. - Company culture and actions don't align, especially lately. People are being laid off without warning. It's a stressful environment even for high performers, as reviews can be dismissed as "inflated". There is no compensation transparency. - No path to career growth for software engineers. No promotions.

Pros: - Good parental and sabbatical benefits. - If you live in a low-cost location, then the salary can be comfortable.

Cons: The leadership is clueless about how to grow revenue, and the company has been going downhill since 2023. There is leadership rot, due to which obvious solutions to some business problems never get implemented. The CEO doesn't believe in data-driven approaches nor in marketing, and that shows in the company culture. Products are launched according to the whims and fancies of a few who think they know what will work, only to discover a few months later that their feature tanked revenue. It is then rolled back. Rinse and repeat multiple times a year. Several silent layoffs happened since 2023, and then in 2025, they laid off 16% of the workforce, which includes tenured and high-performing engineers. The company claims its culture is based on kindness, but it all started going downhill since 2023. CEO worship culture. Internally called Matt-bombs, a single comment from the CEO is enough to change the entire direction of the business unit overnight. Limited personal growth opportunities. There are no promotions or levels. The company spins this as a great thing, but you could end up in the same title for a decade or more. Fine if you plan to never look for another job. Leadership internally recognized this to be a problem and started a few solutions to address them, but in true Automattic style, never saw them through.

Pros: - Great attention to WLB. - Traveling for meetups is fun. - Good salary for non-US contractors. - Sabbaticals and parental leave.

Cons: - Lack of career growth opportunities for ICs besides becoming a team lead. - Team leads are engineers, which sometimes makes for some bad leads. - Constantly shipping the org chart; lack of a consistent product vision. - No stock compensation. - Design is way too siloed.