Pros
Everyone across the company is thoughtful, great at their job, and holds each other to high standards. Codebase is clean, well-organized, and generally high quality. Product is genuinely interesting and has a lot of potential for growth. User enthusiasm is really inspiring, and differentiates us from the bevy of other productivity tools. Business is doing well, and profitability allows us to be thoughtful about growing (and we are trying to grow). Good communication, transparency, and responsiveness from engineering management and company leadership. People like teaching and learning. Office is shoes-off (!), cozy, filled with tasteful household goods, and in a lovely residential area. Health insurance is top-tier. Free lunch in the office (except during global pandemics), and annual recreational offsites for bonding with the whole team. People come from really interesting and diverse backgrounds. Working without shoes allows your toes to fly free. Engineering compensation is highly competitive.
Cons
Lots of bespoke, homegrown technologies — not inherently a con, but does mean there's a steeper learning curve and more surface area to maintain ourselves. As a company, we're still learning how to effectively plan and execute a roadmap, collaborate across teams, and balance feature development with responding to users' needs. During times of normalcy, there's little flexibility for remote work. Hopefully the current pandemic gives us an opportunity to learn how to do it well. Several attempts at recurring team events (board game nights, etc.) have fallen through. I suspect people are less likely to attend because they're working hard and/or have families, and the company is still quite small. Recently there was some turnover without much communication to the company about what happened. Obviously sensitivity and privacy are crucial, but the lack of communication can trigger feelings of unease, like things are being pushed under the rug (regardless of whether or not that's the case). It would be nice to give employees some kind of stipend for working from home.