Vantaggi
Planet provides an opportunity to work on a unique dataset at scale. We have an excellent software organization, and get to work on interesting technical problems with a solid infrastructure foundation. There's also an opportunity to work with and learn from lots of "big names" within the geospatial world. One of my favorite things is the internal "hackweek" twice a year. It's a really neat chance to get to actually work with our data.
Svantaggi
We have a sales culture of misleading customers, writing undeliverable contracts, and blaming engineering. This is largely because we have poor product-market alignment. We've solved the wrong problem, and frankly Sentinel provides better data for many use cases for free. The product organization is at best absent, and at worst severely dysfunctional. In many cases, we experience long hours, high work load, and there's an implied 24/7/365 availability requirement (+ pager duty). "Unlimited vacation" is misleading as a result. Additionally, expect very low pay and little/no raises, though I suspect SF employees may make more out of necessity. If you're considering Planet, you should be willing to take a significant pay cut from your current role, not a match.