After a two-year reboot of a 40-year portfolio tradition, Manhattanville College has moved from a required, one-size-fits-all undergraduate portfolio to a series of developmentally-scaffolded ePortfolio courses. This new approach allows students to reflect upon and integrate their learning at the first-year, sophomore, junior, and senior levels, as well as around Study Abroad, Internship, and Service Learning experiences, thus helping them link their educations to their personal and career goals and aspirations. With the help of faculty, alumni, and employer mentors, students are supported in their transition from high school to college and from school to work, developing a community of practice around reflection, self-assessment, self-presentation, and communication. This paper will examine the use of design thinking as a process guiding program development and revision, as well as look at the unique features of the courses offered at each level of student development.