Pros
So far I have been with Grammarly for the last 7 years. It feels like I have worked at several different companies during this time. The circumstances evolve rapidly and we find ourselves in a new reality every year, and every version of reality has its unique challenges and opportunities. This is true for everyone at Grammarly but for engineering managers especially. Figuring out how to operate on the next level of scale is the most rewarding work. It feels like we have already scaled a couple of orders of magnitude but there is still so much opportunity around. Every team I work and have worked with could double in size and still have enough impactful work on their plate. Most amazingly, there is a guaranteed human touch to everything. A while ago, I had a conversation with my manager about my focus areas. He started it with a "what makes you happy?" question and helped me align my choices with my aspirations first, all other circumstances second. I've come to depend on this approach both in my work and in my expectations from my bosses. There is a lot of respect, support and genuine care between everyone in the company. Did I mention that Grammarly is a rocketship? It is. Don't take my word for it, look at the public announcements about our launches and milestones for the past few years. So, yeah, hop on.
Cons
You certainly have to be willing to work a lot and be open to a lot of changes and adjustments. Is it a con? I don't know :) Makes for an interesting life, for sure.