Pros
The working environment at Ultimate Software starts with the culture that is cultivated by the CEO Scott Scherr who passes it along to all employees during New Hire Orientation when every new employee is brought to at the company's headquarters in Weston, FL. It is a family culture where everyone is treated as an important member and Scott's philosophy which he has stated during several interviews at business conferences; that "if you take care of your employees, then they take care of you". "The important thing is to focus on keeping your employees happy, and focusing on growth per person or growth in annual average productivity". Ultimate Software strives to maintain that culture by providing benefits such as 100% fully paid health care premiums, stock grants to each employee upon hire, 35% match of employees' contributions to their 401(k) with no cap. These are just a few of the perks that keep employees satisfied, wanting to produce and remain loyal to the company. The company's identifying slogan "People First" is more than a slogan. It is a value actively practiced daily.
Cons
The only thing I would say would be a con is that as the company grows, just as in any family situation, sometimes the competition to "get to the top" forces people to forget about the importance of the culture. I have witnessed some backbiting and active undermining from some to move ahead of others. I know this is not unique to Ultimate Software and that as long as employees are human, they bring with them human nature.