Pros
Some of the people who used to work here were awesome, but then they all left and things just got worse and worse after that. So really, no pros.
Cons
Expect to work 80 hours per week and be told it's not enough or that you're letting life get in the way because you ask to have a weekend or two off every now and then. They'll ask you to "wear many hats" but what they really mean is that you will do exactly as they say and that you are lucky to work here. Don't expect to get paid what you're worth by any means. Don't expect your voice to be heard. As soon as a certain team member decides they don't like you, they'll put a target on your back and BOOM, your life is a living hell and you'll either get driven out and leave on your own (which I highly recommend) or get fired. That team member is driving the company into the ground single-handedly. Lastly, this company won't last more than a year at best. I'm surprised they've lasted as long as they have, honestly. They have 2 customers: one who hates the product so much that people quit that organization and cited HighRoads as a reason for leaving, and another who just uses their APIs and avoids the HighRoads UI at all costs. They've already had to take out loans just to pay their employees' salaries. They had 3 rounds of layoffs in less than a year. They've slimmed down to less than 20 employees in-house and their entire development team is offshore in India. Oh, and that team does not work Eastern Time business hours, and they'll expect you to be available anywhere between 6:30am EST to 2am EST to accommodate the Indian team who barely delivers. All the signs are there, the writing is on the wall, the light is most definitely at the end of the tunnel. You, and Highroads, should walk into it and get out now.