In graduate programs such as social work, field education is the signature pedagogy of education. As such, student placement with an appropriate field education agency is critical to ensure academic success and career readiness. A variety of Learning Management System (LMS) and Integrated Planning and Advising Service (IPAS) technologies have been developed to fully integrate technology into the educational system and streamline and improve the learning experience for students, educators, and administrators. Few (if any) of the existing solutions have capabilities to match students with field educators on the basis of an individual student’s completed coursework and area of specialization, as well as field educator needs and opportunities. This paper describes our experience developing a custom LMS/IPAS system—the School of Social Work information System (SSWiS)—that was designed specifically for student learning, faculty advising, and academic administration within our social work graduate program. We present the challenges that motivated the design of the SSWiS before describing the architecture and functionality of our solution. We then discuss our preliminary evaluation results. We conclude with a discussion of the benefits and limitations of our system in the context of today’s technical needs in graduate education in social work and other fields.