Pros
The ideas behind Dakota Software's applications are very interesting. The content that they've spent 25 years creating is their selling point. You'll be very busy - never bored! Small company, so you'll have many jobs. Some people (lower in the ranks) are trying their best to rewrite the software so it functions like people expect 21st century software to function. I learned a lot about different kinds of technology when working there.
Cons
The support and services (implementation) teams have been struggling for years. Sales and R&D think it's a problem with the services department. It's not. The struggles stem from sales making promises to customers that can't be kept. They also stem from the fact that the software is old and dated and buggy. Upgrades only introduce new bugs. Customers have almost no way to customize the software themselves, so they are left waiting and angry. The tools that the services team has are garbage. For all these reasons, turnover in this department is absurdly high. Customers have noticed and are starting to drop off themselves. The president of this company holds power too close and doesn't listen to other people. He has also kept people on board who should have been fired for laziness, lying, sexual harassment, and other serious problems. If you're a person who cares about your work, you will struggle here. If you're lazy, you'll coast! Sales is overpaid and everyone else is underpaid. I genuinely wonder how the company has survived this long, and suspect it will be sold within a few years.