Pros
Great place for new grads who need to get experience with a low barrier to entry. Stock purchase plan was helpful.
Cons
This is a company that will pay you below what other companies will, provide very average benefits and expect you to work nights and weekends. The CIO once gathered his entire department together for an impromptu speech and told us all that we'd be expected to work on weekends due to goals of upper management and if we wanted to work only 40 hours, we can quit and go to Liberty Mutual. The monthly bonus structure paid out exactly once in my 2.5 years. When I had a physical and my doctor found out I was working for Bottomline he said "Oh, that must be why your blood pressure is high" I've had the sales team sell functionality in a product that didn't exist so that it could be used in a way that wasn't intended and my team had to play catch up to this reality. Sales is king in this org.