Pros
Think of Rippling as startup boot camp. And think carefully. If you can hack it, you'll learn a ton, you'll get to build and deliver very cool stuff, and you'll be surrounded by people who are much, much smarter than you. The product is legitimately good, and you will become much, much better at your job. It's an exciting place to work, and you'll feel both proud of what you accomplish and capable of doing anything, anywhere, with that experience in your back pocket. The CEO is genuinely an insanely smart dude. Much of the exec team is as well. That changes a little bit in middle management, as it does everywhere, but Rippling has a very strong vision, a very strong runway, and very strong product-market-fit. The marketing team is crazy strong, but also always almost collapsing—and going through some serious growing pains. But the people are brilliant, and you'll trauma-bond with some genuinely fantastic marketers. If you want to grow your career, I can't think of many places better to do it, but you should probably get a therapist in advance.
Cons
Consider what you want from a job at Rippling before you take a position. And consider that they're Series E, so you're getting (probably) below-market comp and mediocre benefits without the benefit of early-stage equity. As for working there: say goodbye to the rest of your life. You'll get Slacks and emails at 1AM. You'll be lucky to work a 50-hr week (expect 60-80 if you're a SWE). Rippling is sink-or-swim. It is not for everyone, and I would only "recommend" it for a very particular type of person. You'll get next to no support, and you'll be asked to own, build, and deliver results on completely insane timelines. Approval chains are endless and convoluted. Processes are still being built and rebuilt, so expect chaos. Turnover is—proudly—very high, especially in the marketing department. It's not uncommon to get fired within weeks of joining. Expect the standard Silicon Valley nonsense as well. Rippling is a nearly-2000-person company that acts like a 12 person company. The same 10-20 people in leadership make every decision, and unless you have one of them on your side you'll find it tough going. The culture at Rippling has changed a lot in the last year—and not for the better. It's less collaborative and even more cutthroat. Expect heads to keep rolling for a while longer. If you are considering management: because teams operate so independently, there is a fair amount of backstabbing, arguing, and one-upping. You should expect to be fighting for relevancy (and budget) at all times, so find people with influence and get them in your corner quickly. My advice: have a goal, and have a plan to get what you want and get out. Have thick skin. Expect high turnover. Assume you're expendable. And be very careful about trusting anything you're told.