Pros
InsightSquared is truly the best place I've ever worked in my career. My favorite parts about IS2 are the culture, the perks and the people. We get free lunch daily (2 options!), tons of swag, kegs, ping pong, corn-hole, gym reimbursements, unlimited vacation policy and tons of other best in class perks. My fellow employees are closer to being my best friends/family than coworkers. We have a true work hard, play hard mentality. The executive team is transparent and hardworking, and cares about every individual that works here. They have a true open door policy, and are always willing to help out where they can. If you have the ability to work at this company, you should 100% jump at the opportunity.
Cons
It's hard to think of any cons for working at InsightSquared. There is a good work-life balance, but it is a small tech company, so be ready for there to be a lot of things on your plate. InsightSquared is a fast-paced environment, which can mean less structure than a traditional corporate environment, so make sure that works with what you want to get out of a position.