Pros
You can still find some of the original employees at Upwind; they extremely talented and very friendly. If you're in sales, you can coast on Upwind's market momentum for a few quarters before the company starts failing.
Cons
Generally, terrible executive management that breeds an incredibly toxic culture. Upwind's toxic culture is ruining the company. It is a master class in that bad culture will eventually destroy a company. Unless you are very desperate for work, I recommend that you avoid this place. Additional details: - 24/7 work is expected at Upwind, including holidays, weekends, and PTO. You will burn out at Upwind; it's not a matter of if, it's a matter of when. - There is no reasonable hope for career advancement at Upwind. Any promotions are based how many hours are worked, rather than impact. If you regularly work until 2am, over major holidays, and on PTO, you will likely get promoted. If you want a life, expect to be demoted, or eventually, fired. Check out the executives' Linkedin posts bragging about how Upwinders are working over the holidays - it's a real thing! - Upwind’s product innovation has stopped as many of the key product employees have left. - Upper management is very egotistical and self-interested, mostly because they have to be in order to appeal to the CEO. More on that later. - All the cultural values that Upwind says they practice are a falsehood. - The CEO frequently throws emotionally charged temper tantrums, and employees walk on eggshells to avoid drawing his rage. The CEO's answer to most company questions will be “speed”, which is code word for “crack the whip on the employees harder”. Do some searching on Linkedin to see how many times the world "speed" is mentioned in association with Upwind! - Upper management is generally misogynistic. My female coworkers caught most of the yelling for no particular reason, in my view. - Upwind is hiring a lot of questionable new hires who got their jobs out of nepotism. Upwind is pushing out their talented original hires who got them to where they are in the first place. On the plus side, if you're a headhunter, it's open season for any of the original employees - go get 'em!! - Upwind wants “yes men”. If you go to work here, do not voice any ideas. Just do what they tell you to do. Pushing back on anything is considered a taboo at Upwind.