Pros
The work-life balance is pretty great with a take time as you need it mentality. You also do get to work with a ton of very bright people and the team culture is about as good as you'll find anywhere else. Thankfully, Woot is finally going back to what made woot great to begin with: fewer, better deals.
Cons
As a developer, coding is a daily struggle. The development environments are extremely fickle and break constantly. The testing environments are not sufficient to test any changes and lead to tons of changes being rolled back. The majority of our tools and scripts are outdated, tribal knowledge is vanishing by the day, and project deadlines might as well be chosen randomly. Decision making seems perpetually done in a panicked state, with priorities changing with the wind. Software managers are ex-devs but frequently act as Project Managers leading to a fairly large disconnect between management and the development team. Quick results are valued much more highly than doing something slowly and correctly. Woot's culture is meant to be quirky and fun, but this frequently crosses the line to immaturity and an excuse for a poor experience. Fired all the writers and the impact on the site is palpable.