Internal process's lack maturity. A lot of company silos where one department does not confer with others. Zero focus on how decisions and changes impact users, very little testing of system configuration changes. HR/People team is rigid and unwilling to address Salary and Position changes outside of their yearly cycle.
Messy 3rd Party HealthCare provider with poor customer service.
A startup mentality with attention paid to optimizing and unifying services, process, and procedures across the company.
Support 3 separate OS systems poorly.
Tendency to adopt new services on a whim when existing services are already being used. They do not quit the legacy service when signing up for new one.