Caltrans has traditionally focused on designing, building, and maintaining California’s large freeway network. Lately, a stronger focus is being placed on real time transportation network operation, which requires the use of real time data and decision support software tools. This transition represents a cultural shift for Caltrans, and its organizational structures and staffing processes are not yet in place to support the effort. This report explores major impediments to hiring data analysts and software engineers, including lack of understanding among current management personnel in regard to the need for data analysts and software engineers, barriers for Caltrans Operations to directly hire IT/software personnel, lack of interest among Caltrans engineering unions to include software engineers as members, a general belief that software engineers are not “real” engineers, and concern that the state will not be able to hire software engineers due to high salary demands. Opportunities for addressing barriers include developing appropriate recruitment strategies for software related positions, educating agency personnel on the need for data analysis and software skills, changing the requirements for positions in Caltrans traffic operations, and establishing a management team to coordinate and support these efforts.