Pros
The company has been around for many years and continually re-invests in it's products and employees. The product itself is extensive with a large feature set and a large target market. There has been a shift in staff over the past few years and the people here now are typically great to work with and committed not only product but also the company. Windward as a company is also usually very loyal to it's employees. Once you have been with the company for over a year you are typically looked at as family, with all the positives and negatives that go along with being a family member. Some perks I've found are having a flexible schedule, a good social area downstairs and of course location(there are offices in downtown Chicago and Beachside in Penticton). The open door policy of management is also a great perk as it helps you feel connected to where Windward is going as a business.
Cons
It's a medium size company. That's really the core con. The company is growing but has growing pains at times. While it gets a lot of the big things right Windward struggles with some of the smaller but just as important details like communication. Change is not easy and working at a company like this means you need to be prepared for changes and sometimes mistakes.