Pros
Amazing, talented people (but many are gone).
Great pay, decent benefits.
Work-life balance was usually pretty good for a startup.
Cons
4 rounds of layoffs in 2 years due to over-hiring and bad decisions. CEO kept claiming there were years worth of runway, then more cuts would happen a few months later. Senior management were never transparent about the health of the company.
Company was acquired earlier this year. New owners are stuffing the product full of cross-sell features to try and rush toward profitability, and the brand is suffering. Developers are stretched thin trying to meet aggressive deadlines, and shipping buggy, barely tested code. At this point Engineering is a skeleton crew. It feels unlikely that Extra will be around in a year.