Pros
Great culture I'm sure the IPO will go great The product, by all accounts, is fantastic
Cons
I get the mentality needed for a startup company, but they use it as an excuse to be negligent in their operations and business dealings. It is run like an old boy's club from the 1950s. If you are not part of the sales organization you might as well not exist. If you are not sales, I promise you will either (a) mentally check out and begin punching the clock or (b) do the ethical thing and quit. After I started with my current employer they told me that they hired me "despite the fact I worked at Avalara"; that working at Avalara was a RED FLAG to them! TERRIBLE benefits (401k match and vacation are criminal); you're not getting in on the ground floor any more - your stock options will not make up the difference.