For my first two years, this list would have been small. My last three years have been some of the frustrating experiences of my life. The first problem was scaling and growth. The company grew considerably since I was hired and I do not believe senior management was prepared for such quick growth. Moreover, when Hyland acquired Lexmark's Perceptive (which felt much more like a merger) the true cronyism of Hyland's management structure came out. It turns out that for most employees, there is no growth beyond title changes, with little change in day-to-day work unless you become well-loved by several senior managers or VPs.
With the growth came coasting. Hyland simply could not maintain the culture I was used to with so many people. I noticed employee engagement drop, people caring less about outcomes, and general apathy among my peers. I believe this also came from senior management shutting down any ideas or feedback that they didn't come up with. I also saw this from first-tier management who really *wanted* to and *tried* to help their team, with no help from senior management.
The product does not scale. The architecture is *very* monolithic and inflexible. While the company is trying to fix this, they are failing left and right. Recently products that were in development for over two years were simply canceled and people layed off! There isn't a clear direction for the future and efforts to modernize the software have been totally muddied: every senior manager has a different idea that changes week to week. We have wasted many weeks spinning our wheels while we move from one technology to another, accomplishing nothing.
