Automattic

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

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.

Stop giving leadership roles to the same few people who are responsible for the current state of the company.

Look at your maisons – do you have anyone new in the ranks?