Pros: Remote work, but remote and hybrid opportunities are everywhere still if you're looking beyond the largest few companies.

Cons: It's hard to properly communicate how career-limiting a long stint at Automattic can be for a software engineer. Automattic's tech stack was outdated 10 years ago, and there's been little movement since then. They're really good at running simplistic WordPress sites performantly, but anything beyond that is a hot mess. Good luck passing a system design interview when you're drawing on the experience of hacking some code into the WPCOM monolith, crossing your fingers, and hoping for the best (did I mention there's no test environment or system test capabilities?). And I'm not suggesting resume-driven design here. The tech stack and tooling has a real concrete impact on engineering velocity and innovation. Many product-level decisions died in ideation because we didn't have an immediate path forward and knew advocating it with Systems would be a job killer. The impact to the business and product quality is incalculable. As an aside, I'll mention that I have no problem with PHP. Plenty of companies value PHP, but Automattic is not using modern frameworks and rarely using good design patterns. Even many WordPress companies are doing better. The teams are facing some incredible engineering challenges. It's incredibly hard to create and scale features supporting millions of sites all running in their own environments alongside any number of custom plugins. Quality is almost impossible to control given the myriad of environments and poor access to critical metrics. I don't believe there is a profitable solution that allows continued growth. There's a reason the whole industry has moved to SaaS. Without crystal clear focus/strategy and strong leadership, it's an intractable problem. Unfortunately, Automattic fully lacks the necessary strategic and technical leadership to forge ahead successfully. Since there's almost no built-in career growth here, Automattic's handbook will tell you to "choose your own adventure" in your career here: choose wisely and skip Automattic all together. You cannot and will not do the best work of your career here.

Pros: Open culture in resolving issues and improving communications. Global compensation for similar jobs.

Cons: Complicated and complex code resources. Scattered documentation and information for the system.

Pros: - Decent benefits for US-based roles that align with international standard minimums. - Remote work environment, asynchronous for some support roles, with the expectation of 24/7 availability for most other roles.

Cons: - Product leadership is completely absent. Product teams are literally led by engineering and infrastructure roles, naturally resulting in hostile product offerings with poor performance that users hate. - Zero job security. Entire teams just disappear overnight without explanation. - Lots of technological dead ends. Absolutely no innovation. Internal tools look and feel like they’re from 2014. External-facing tech using PHP + Javascript is just barely keeping up with competition – the primary product strategy is just to “be better than Vercel.” - A tremendous amount of unleveraged overhead roles in HR, Leadership, and Developer Experience, all contributing to broken internal processes for hiring, feedback, and compensation. For ICs in engineering, these roles heavily restrict any meaningful agency and impact. - American-centric “work harder, not smarter” SV grind culture still exists. More hours === more productivity. For foreign labor markets, local labor laws protecting working hours and hours per week are written out of contracts entirely. - Very long hours for high-level engineering roles. No room for agency or impact beyond just fixing bugs in code from others that have been let go before you. - Anti-inclusive: DEI candidates, seriously: do not waste your time. Your experience will be painful. Just say 'yikes' and move on.