Pros
Flexibility is a major bonus and working from home. Usually don't feel like no one is watching over your shoulder. You are essentially left to it, sometimes it's bad, other times it's great. The company trusts their employees to do what they should - unfortunately it doesn't work at all times. Generally the teams I have met are friendly. Few people in Upland are at the core of the company in that they are like sticky tape, holding everything else together. Without their leadership and drive, the company would struggle to run well.
Cons
Disjointed systems due to the nature of the acquisition business. Poor data literacy in most people. Cumbersome integration processes. Key focus on sales and utilisation can make you feel like a factory machine worker (most likely due to the differences between American vs UK cultures). Poor review of performance and staff skills, an imbalance of abilities affects general workflow. Products can't compare with competition, bug fixes and product improvements take too long - company needs to think ways of preventing only few people becoming an expert about a particular product, and having others guess about how something works.