Prós
Joining a small start up can be scary but it also has its perks. One of the biggest perks is the autonomy you can get to learn and grow your profession i.e. create new processes, provide feedback to invoke change, and much more. RudderStack allows you the autonomy to truly experience the job you signed up for rather than just putting you into a spot and have you row the boat. You are the driver, rower, sail, and any other cheesy boat analogy you can think of.
Contras
It's a start up: There are growing pains, missing processes, you name it. You can view that as a con but also an opportunity to make an immediate impact. You may not get the warm and fuzzy 1:1's or may not even get a lot of direction - so you have to be a self starter or else you may find yourself in trouble. The hard part of any company being remote first is getting the feeling of culture compared to other companies - RudderStack is also growing so fast that it feels like culture is just the last thing on its mind. Again, welcome to a start up.