We've been using this software since it was introduced in 1999! It's easy enough that our managers have learned how to navigate through their own business needs without any training from us at all - we just train them when they ask questions or need help with something specific (which is often).
I like being able to see what my drivers are doing while away so much time off of paperwork/paper requests if needed as well. The only thing about TWM that could be improved would probably be some better integration into other systems such as accounting programs etc., but even then there isn't anything wrong really except maybe ease up on updates sometimes because things get buggy occasionally? Just keep an eye out though, once those bugs come along eventually everything will work again after updating which usually fixes most issues anyway :D Definitely recommend taking advantage of live chat support whenever possible too cause not.