Many educators and education leaders have found implementing districtwide programming at the secondary level challenging. High schools are more organizationally complex than elementary schools (Grubb, 2010). High school teachers are deeply entrenched in subject specialties and tend to be resistant to change. This article describes how the Greater Essex County District School Board, in Ontario, Canada, struggled in 2013 to implement a program called the Specialist High Skills Major, which offers students the ability to customize their high school experience and focus on skills relevant to the world of work. Students can specialize in 19 different sectors, ranging from arts and culture to transportation. In 2013, there were 43 programs in the district's 16 high schools, yet student enrollment in the program was average to low. Only 8% of the district's 11th- and 12th-grade students were enrolled and, of those, only 4% completed the program -- one of the worst completion rates in the province. In four short years, that changed completely. The district gained 11 new Specialist High Skills Major programs, enrollment rose from 8% to 20%, and the program's completion rate rose from 4% to 81%. This change did not happen overnight, nor was it by accident. Strategic planning and focus, a modification of Michael Fullan's (2007) framework for program implementation, and lessons learned from an evaluation of the program province-wide (Segedin, 2013) were the catalysts for this growth. The author maintains that by following a framework similar to the one Essex used, other school districts may experience similar success from applying the five components that arose from the experience of Greater Essex. They are: (1) Create a need; (2) Provide clarity; (3) Minimize complexity; (4) Emphasize quality, and (5) Prioritize shared leadership. While each of the five is significant alone, the steady growth of this program required a consistent and simultaneous focus on them all. Each component is detailed in this article.