Electronic portfolios are a student-centered outcomes-based assessment regime involving learners in the gathering, selection, and organization of artifacts synthesized into a compilation purposed to demonstrate knowledge, skills, and/or achievements supported by reflections that articulate the relevance, credibility, and meaning of the artifacts being presented. Electronic portfolios have been found to be a valid way to document student progress, encourage student involvement in assessment, showcase student work samples, promote students professionally, and provide a method of student learning outcomes and curriculum evaluation. However, electronic portfolio adoption represents a sizable commitment that is influenced by a number of variables and that requires foresight as well as a thoughtful strategy. This paper presents a model for selecting, designing, and implementing an electronic portfolio project and illustrates its application through the presentation of a detailed case study of a successfully implemented and ongoing electronic portfolio project used as a comprehensive assessment measure to determine degree mastery in the Department of Business, Management, and Accounting at the University of Maryland Eastern Shore. The model introduced in this paper is known as the Pentagonal E-Portfolio Model, named such for its five levels: 1) Level 1 - Identification of Needs; 2) Level 2 - Determination, Assessment, & Budgeting; 3) Level 3 - System Selection and Strategic Planning; 4) Level 4 - Development; and 5) Level 5 - Implementation and Continuation.