Pros
In general, great, talented people who are very invested in making the product and company live up to its potential. Work is remote and flexible (though you can work and get snacks in one of the hub offices). My compensation package was very fair.
Cons
Disorganized, constantly changed priorities the whole time I worked there, and no one seemed to be in charge. "Students first" value is at odds with the product priorities. Some pretty glaring (and fundamental) product questions were glossed over. Plus the weird layoff situation where people were quite clearly laid off - NOT for performance issues - but leadership insists it wasn't layoffs. Basically, when the going got tough, Handshake decided to lay folks off, blame them, then take away benefits for current staff (a company-wide week off on July 4th is no longer offered) and slap a "high performance culture" label on everything.