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Automattic's tech stack was outdated 10 years ago, and there's been little movement since then.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.
