Pros
Awesome product that is really helping folks. Great culture with folks really committed to spreading meditation. Perks and people are the best.
Cons
Management is truly incompetent and tone-deaf on a lot of issues. The CEO has zero tech experience and it is painfully apparent to anyone that anyone that watches him operate. He makes decisions at the last minute that send everyone scrambling and he has little to no focus. Much of the time at the company(including time spent by other execs) is spent managing up because of that. Moreover, very few of the senior management have start-up backgrounds and that really impedes the work. Management also does a terrible job communicating information around layoffs/firings and then pats itself on the back for handling them well (in their mind). Although it's a company that prides itself on its culture, the frequent and unannounced firings give Headspace a chaotic Hunger Games type feeling.