Pros
Rippling is an amazing company for people who love building products, engineering challenges and take initiatives in proposing solutions. One of our leadership principle is "challenge each other directly", which means feel free to counter ideas of other people respectfully. I have spent more than 5 years at this company and worked under many teams. I have always felt empowered to convey my concerns to the management and they do take an effort to make the situation better. We prefer honest dialogue over gossip. Though there is bureaucracy, there are enough good people in the organization to help you navigate through it.
Cons
It is currently in a phase which is somewhere between a startup and an enterprise. So, it shows traits of both. Face-paced yet restrictive on a lot of policies. Rippling is not a place where you can join and chill for a few months before producing actual work. We are not that laid back (and hopefully we never become like that!).