Middle (Director Level) Management - Several of whom don't know the key systems and business processes of which they manage leading to mayhem coupled with erratic goals and unrealistic expectations.
Top-Heavy Management - Similar to other workplaces in South Florida (and perhaps across the country as well during these times) it seems like Ultimate is a company of have and have nots. Company parking lots are a mixture of high end luxury vehicles coupled with economy cars and beaters. The shrinking corporate 'middle class'.
Silo'ed Business Units - Not unique to Ultimate Software, but nevertheless communication between certain departments is an issue.
Morale - Though very high as stated in the previous section, one gets the feeling that if it weren't for Ultimate Software picking up employee health insurance coverage, it might just be another place to work and some folks would definately flock elsewhere. Some employees feel locked into Ultimate for this reason.
"Hot Potato" Departments - Workplace Support and Sales Operations (not Sales per se). Both are plagued with bad management, low morale and turnover.
Possible Aquisition - Though not a Con if you are a shareholder, it is an area of concern for many as the SAAS software Market has been seeing an uptick in companies buying up others. A clumsily written denial email (responding to such reports) by Scott Scherr to employees earlier this year has only fueled the speculation.