Vantaggi
The health benefits were great, and early on, the company was a 'presume good intent' company. I would say that is now just a smokescreen to allow negative things and put a pretty bow on them. I do, however, love startup life.
Svantaggi
The culture has changed a great deal, as it wont to do with a startup, but it's changing in the wrong direction. Because it is growing so fast, people are being promoted who are not even remotely ready to manage people, which creates issues down the pipeline. The biggest con I can see is how much of the customer service is being sent to the Philippines. The ClassPass voice used to mean something, and was recognizable to their members, but they are now hiring people who clearly aren't a good fit, merely to save on costs and benefits. Sadly, it's the members who pay for that in difficult service.