Pros
Most employees are good people with good intentions. Middle management is pretty good about not micromanaging and promoting work/life balance. The benefits are better than what most companies would provide. The product has a good reputation and the name is respected in the industry.
Cons
The last 2 years have been stressful on the entire staff with all the change and expansion plan. A lot of strange decisions strategically with management roles and responsibilities without much communication as to why those decisions were made. The Americas Leadership team is mostly very solid and they should have been given far more control over the way business is handled in the Americas. HQ has been increasingly controlling over the regions and even down into different departments. Travel was recently cut almost entirely so in person events were all cancelled which were always one of the best things about working for Milestone. The recent layoffs could have been avoided and should never have happened. This put a lot of great people in a horrible position and the whole thing was not handled well at all. Loyalty, dedication, and ambition might get you somewhere but it might also get you laid off apparently.