Pros
The best thing about working at UpKeep is the company culture, and not in a gimmicky way. Management legitimately cares about you as a person, the unlimited PTO is legit and encouraged, and above all I am trusted to get my work done without someone breathing down my neck. It's a fully remote job, and upper management works hard to make sure we have plenty of opportunity to feel like we're still able to connect with our teammates. At least in my department, we have a very clear and measurable path forward in our careers, and my manager and I talk about where I want my career to go both at UpKeep and beyond it. Expectations for me are very clear, which helps me keep my head on straight while working.
Cons
If you prefer an in-person environment and are not in LA, this isn't the place for you. There is an HQ, but from what I understand it's under-utilized since the pandemic. There have been some funky rules around timing for promotions and pay increases, but it seems like those are getting ironed out as time goes on.
