Pros
It is amazing to see (and feel) how much everyone at Help Scout cares about the customer, the product, and each other. Working on a remote team can be hard, and at times a little lonely. However, the People Ops team have done a damn fine job in making sure everyone feels connected. The friendliness of the team (because everyone here is incredibly nice) also makes you feel like you have people you can talk to. I've never experienced (non-work) Slack team chat rooms so full of life, it's great! Because of my unique role in the company, I was privileged enough to be able to experiment and explore concepts that go beyond Help Scout, specifically open-source based code. Not only was my team, my manager (and heck, everyone in the company) supportive of this effort, but they were also excited and they encouraging.
Cons
I think the only con is it might be tough if you're hired as a remote worker, and you've never had remote working experience before. By remote working experience, I don't mean you get to work at home on Fridays kind of thing.. I mean you work by yourself almost 100% of the time (with the exception of team retreats). Remote culture is embraced here, along with all the responsibilities of being remote. However, the team is exceptionally understanding and supportive!