Faculty from two universities in Florida and Ohio designed, developed, and implemented programs to work with youth from their respective service regions to support college and career readiness initiatives. Both programs were directed by university faculty and utilized university resources to support K-12 students' career development skills. In this paper, we examine the programs' designs, implementations, and results; we include feedback from students, school personnel, and local stakeholders. Attentive to results and the relevant literature, we hope to ignite a long-term discussion on how universities can create effective outreach programs that help support student transitions from high school to college, or directly into a career.