The surface transportation maintenance operations workforce faces major changes as experienced employees retire in large numbers and younger employees replace them. The generational differences are well documented, particularly as to training and career development, thus requiring new approaches to ensure a proficient and productive workforce. Additionally, the job duties and responsibilities are changing due to advanced technologies and more stringent regulations. Both private and public sectors recognize this and are adapting to a more diverse workforce that must be highly competent, adaptable, and versatile. Determining what training is needed for the current workforce and how that training is delivered are essential. At the same time, it is vital to create a “pipeline” of future workers, by promoting this discipline as a rewarding career. This paper will explore innovative training and career development strategies to build and sustain highly effective maintenance operations workforces.